991:
672:
977:
584:
291:. Also called "banana borane", it exists as a dimer. It can be distilled without decomposition at 195 °C (12mm Hg). Reactions with 9-BBN typically occur at 60â80 °C, with most alkenes reacting within one hour. Tetrasubstituted alkenes add 9-BBN at elevated temperature. Hydroboration of alkenes with 9-BBN proceeds with excellent regioselectivity. It is more sensitive to steric differences than Sia
3374:
3225:
3293:
3130:
31:
496:
173:
892:α-Halo enolates are common nucleophiles in borane reorganization. After nucleophilic attack at boron, the resulting ketoboronate eliminates the halogen and tautomerizes to a neutral enolborane. A functionalized carbonyl compound then results from protonolysis, or quenching with other electrophiles:
857:
An organic group's migration propensity depends on its ability to stabilize negative charge: alkynyl > aryl â alkenyl > primary alkyl > secondary alkyl > tertiary alkyl. Bis(norbornyl)borane and 9-BBN are often hydroboration reagents for this reason â only the hydroborated olefin is
242:
Dialkylboranes are also rare for small alkyl groups. One common way of preparing them is the reduction of dialkylhalogenoboranes with metal hydrides. An important synthetic application using such dialkylboranes, such as diethylborane, is the transmetallation of the organoboron compounds to form
278:
BH. It also is a dimer. Owing to its steric bulk, it selectively hydroborates less hindered, usually terminal alkenes in the presence of more substituted alkenes. Disiamylborane must be freshly prepared as its solutions can only be stored at 0 °C for a few hours. Dicyclohexylborane
2116:
839:
B) is their susceptibility to reorganization. These compounds possess boronâcarbon bonds polarized toward carbon. The boron-attached carbon is nucleophilic; in borates, the nucleophicity suffices for intermolecular transfer to an electrophile.
2133:
Vedejs, E.; Chapman, R. W.; Fields, S. C.; Lin, S.; Schrimpf, M. R. (1995). "Conversion of
Arylboronic Acids into Potassium Aryltrifluoroborates: Convenient Precursors of Arylboron Difluoride Lewis Acids".
1051:
Treatment of an alkenylborane with iodine or bromine induces migration of a boron-attached organic group. Alkynyl groups migrate selectively, forming enynes after treatment with sodium acetate and hydrogen peroxide:
2515:
Nicolaou, K. C.; Sarabia, F.; Ninkovic, S.; Finlay, M. R. V.; Boddy, C. N. C. (1998). "Probing the Ring Size of
Epothilones: Total Synthesis of 14-, 15-, 17-, and 18 Epothilones A".
2077:
1732:
Dodd, D.S.; Ochlschlager, A. C. (1992). "Synthesis of inhibitors of 2,3-oxidosqualene-lanosterol cyclase: conjugate addition of organocuprates to N-(carbobenzyloxy)-3-carbomethoxy-5,6-dihydro-4-pyridone".
922:
Diazoesters and diazoketones remove the requirement for external base. α,α'-Dihalo enolates react with boranes to form α-halo carbonyl compounds that can be further functionalized at the α position.
1242:
112:-unsaturated borates and borates with an α leaving group are highly susceptible to intramolecular 1,2-migration of a group from boron to the electrophilic α position. Oxidation or
1468:
Bartlett, Ruth A.; Dias, H. V. Rasika; Olmstead, Marilyn M.; Power, Philip P.; Weese, Kenneth J. (1990). "Synthesis of the monomeric HBtrip
877:, deboronating in favor of a proton. Consequently, organoboranes are easily removed from an alkane or alkene substrate, as in the second step of this olefin synthesis:
1635:
Boudier, A.; Hupe, E.; Knochel, P. (2000). "Highly
Diastereoselective Synthesis of Monocyclic and Bicyclic Secondary Diorganozinc Reagents with Defined Configuration".
2808:
1608:
Brown, H. C.; Kulkarni, S. U. (1981). "Organoboranes: XXV. Hydridation of dialkylhaloboranes. New practical syntheses of dialkylboranes under mild conditions".
1321:
against acyl halides. Here, the borate was generated from tri(cyclopentyl)borane and phenyllithium; the three cyclopentyl groups do not significantly migrate:
874:
781:
from boron to the carbonyl carbon. For example, homologated primary alcohols result from organoboranes, carbon monoxide, and a reducing agent (here,
1670:
Hupe, E.; Knochel, P. (2001). "Stereoselective
Synthesis of Secondary Organozinc Reagents and Their Reaction with Heteroatomic Electrophiles".
2543:
Batey, Robert A.; Quach Tan D.; Shen Ming; Thadani, Avinash N.; Smil, David V.; Li Sze-Wan; MacKay, D. Bruce (2002).
2529:
1302:
Tertiary alcohols with two identical groups attached to the alcohol carbon may be synthesized through an alkynylborane double migration:
2801:
1056:
1705:
Pelter, A.; Singaram, S.; Brown, H. C. (1983). "The
Dimesitylboron Group in Organic Chemistry. 6 Hydroborations with dimesitylborane".
2499:
1820:
Segawa
Yasutomo; Yamashita Makoto; Nozaki Kyoko (2006). "Boryllithium: Isolation, Characterization, and Reactivity as a Boryl Anion".
1357:
1296:
789:
189:
2220:
1808:
1784:
1592:
1575:
Dhar, Raj K.; Josyula, Kanth V. B.; Todd, Robert; Gagare, Pravin D.; Ramachandran, Veeraraghavan (2001). "Diisopinocampheylborane".
1535:
1423:
1361:
1325:
1306:
1110:
1045:
916:
909:
270:). It reacts only slowly with simple terminal alkenes. It adds to alkynes to give alkenylboranes. Among hindered dialkylboranes is
1648:
896:
881:
851:
808:
1003:
820:
2164:"Organotrifluoroborates and Monocoordinated Palladium Complexes as CatalystsâA Perfect Combination for SuzukiâMiyaura Coupling"
2033:; Dewhurst, Rian D. (2013-03-25). "Single, Double, Triple Bonds and Chains: The Formation of Electron-Precise B-B Bonds".
1548:
Negishi, Ei-Ichi; Brown, Herbert C. (1974). "Thexylborane-A Highly
Versatile Reagent for Organic Synthesis via Hydroboration".
710:
can be visualized as a square with the corners occupied by carbon, carbon, hydrogen and boron, maximizing overlap between the
116:
of the resulting organoboranes generates many organic products, including alcohols, carbonyl compounds, alkenes, and halides.
3506:
2794:
2016:
1878:
1037:
yields haloalkanes. With excess base, two of the three alkyl groups attached to the boron atom may convert to halide, but
188:. These compounds are catalysts, reagents, and synthetic intermediates. The trialkyl and triaryl derivatives feature a
623:
847:
to an electrophilic carbon attached to boron, especially if that carbon is unsaturated or bears a good leaving group:
565:
132:
2545:"Organoboron compounds as mild nucleophiles in Lewis acid- and transition metal-catalyzed CâC bond-forming reactions"
3363:
3358:
3353:
3348:
3343:
3338:
3333:
3328:
3323:
3318:
3313:
3308:
3298:
3241:
3135:
3056:
3051:
2908:
733:
207:
Monoalkyl boranes are relatively rare. When the alkyl group is small, such as methyl, the monoalkylboranes tend to
211:
to give mixtures of diborane and di- and trialkylboranes. Monoalkylboranes typically exist as dimers of the form
3399:
3101:
3071:
3061:
3041:
3029:
2997:
2962:
2930:
2898:
2893:
2853:
843:
Boranes alone are generally not nucleophilic enough to transfer an R group intermolecularly. Instead, the group
692:
2868:
2832:
2786:
3444:
3439:
3434:
3429:
3424:
3419:
3414:
3409:
3404:
3389:
3379:
3230:
3205:
3200:
3185:
3170:
3150:
3145:
3096:
3024:
3007:
2957:
2952:
2947:
2942:
2918:
2878:
1350:
443:
1892:
Paetzold, Peter; Englert, Ulli; Finger, Rudolf; Schmitz, Thomas; Tapper, Alexander; Ziembinski, Ralf (2004).
399:, boron replaces one CH center in benzene. Borabenzene and derivatives invariably appear as adducts, e.g., C
3394:
3384:
3195:
3180:
3165:
3155:
3140:
3081:
3066:
3046:
3036:
3017:
3012:
3002:
2992:
2935:
2903:
1292:
Homologated primary alcohols result from the treatment of organoboranes with carbon monoxide and a hydride:
236:
208:
105:
81:
2873:
2863:
128:
2.55 for carbon and 2.04 for boron). Alkyl boron compounds are in general stable, though easily oxidized.
3303:
3218:
3160:
3123:
3118:
3106:
3086:
3076:
2982:
2977:
2972:
2913:
2888:
2660:
2648:
1969:
1343:
759:
546:
3111:
2923:
2848:
2168:
1346:
1318:
966:
862:
661:
902:
Because the migration is stereospecific, this method synthesizes enantiopure α-alkyl or -aryl ketones.
535:
359:. Such clusters have many organic derivatives. One example is and its radical derivative . Related
3190:
3175:
2987:
2967:
1831:
865:) terminus. The resulting reorganized borane can then be oxidized or protolyzed to a final product.
657:
379:. Carboranes have few commercial applications. Anionic derivatives such as , called dicarbollides,
2665:
732:
improves that ratio for cyclic boron-containing reagents. One common cyclic organoboron reagent is
3091:
2030:
1973:
1268:
1007:
950:
352:
324:
224:
990:
671:
2678:
2567:
1855:
954:
782:
707:
489:
54:
1929:; Malacria, M.; LacĂŽte, E. (2011). "Synthesis and Reactions of N-Heterocyclic Carbene Boranes".
2544:
2773:
2755:
2495:
2482:
2216:
2194:
2108:
2100:
2058:
2050:
1993:
1976:; Robinson, Gregory H. (2007). "A Stable Neutral Diborene Containing a B=B Double Bond".
1946:
1926:
1847:
1822:
1804:
1780:
1687:
1652:
1588:
1531:
1419:
1011:
976:
778:
696:
415:
384:
360:
343:, debatably not an organoboron compound, is an intermediate in sodium borohydride production.
144:
125:
85:
2763:
2745:
2670:
2559:
2525:
2487:
2184:
2176:
2144:
2092:
2042:
1985:
1938:
1905:
1839:
1742:
1714:
1679:
1644:
1617:
1580:
1557:
1509:
1452:
703:
635:
561:
462:
340:
66:
1873:
1076:
1072:
1068:
774:
770:
627:
336:
957:. The reaction is much slower with ketones than aldehydes. For example, in Nicolaou's
492:
are known The unusual compound was prepared by reduction of a boron-bromide precursor:
1964:
Wang
Yuzhong; Quillian, Brandon; Wei Pingrong; Chaitanya, S. Wannere; Xie Yaoming;
1835:
861:
Migration retains configuration at the migrant carbon and inverts it at the (presumably
2768:
2733:
2189:
2163:
1339:
1264:
1038:
1019:
729:
619:
557:
271:
1718:
1621:
3500:
3463:
2644:
2136:
2011:
1965:
943:
844:
724:) equivalents converts only 33% of the starting olefin to product â boron-containing
684:
485:
466:
328:
201:
93:
89:
17:
2682:
2571:
1859:
1336:
Organoboron chemistry is mainly of commercial value in the pharmaceutical industry.
1276:
1256:
1088:
962:
649:
356:
216:
140:
113:
101:
1584:
2651:(1995). "Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds".
1874:
Attacks: Electropositive element pressed into action as nucleophilic boryllithium
2491:
1456:
1440:
1096:
1084:
947:
931:
595:
591:
583:
577:
515:
511:
396:
227:: A chiral example is monoisopinocampheylborane. Although often written as IpcBH
156:
148:
97:
2750:
2419:
Brown, H. C.; Rogic, M. M.; Rathke, M. W.; Kabalka, G. W.
1055:
983:
Trifluoroborate salts are stabler than boronic acids and selectively alkylate
970:
958:
755:
751:
745:
438:
193:
136:
30:
2759:
2530:
10.1002/(sici)1521-3773(19980202)37:1/2<81::aid-anie81>3.0.co;2-c
2104:
2076:
Arrowsmith, Merle; Braunschweig, Holger; Stennett, Tom E. (2017-01-02).
2054:
961:
synthesis, asymmetric allylboration (with an allylborane derived from chiral
2563:
2078:"Formation and Reactivity of Electron-Precise BâB Single and Multiple Bonds"
1843:
1295:
1260:
1104:
788:
725:
714:
639:
364:
246:
Some diaryl and dialkylboranes are well known. Dimesitylborane is a dimer (C
196:. Except a few bulky derivatives, the hydrides (n = 1 or 2) dimerize, like
2777:
2198:
2180:
2112:
2096:
2062:
2046:
1997:
1950:
1942:
1910:
1893:
1851:
1691:
1656:
1801:
Boronic Acids: Preparation, Applications in
Organic Synthesis and Medicine
1649:
10.1002/1521-3773(20000703)39:13<2294::AID-ANIE2294>3.0.CO;2-J
495:
422:, has not been isolated, but substituted derivatives (boroles) are known.
172:
1894:"Reactions at the Boron-Carbon Double Bond of Methyl(methylidene)boranes"
1561:
1272:
1015:
984:
935:
754:
reactions produce an organoboron compound from aliphatic or aromatic C-H
602:
455:
197:
2674:
2408:
The
Organic Compounds of Boron, Aluminium, Gallium, Indium, and Thallium
2148:
1762:
Hydroboration and Organic Synthesis : 9-Borabicyclo Nonane (9-BBN)
1746:
1513:
1324:
1305:
1044:
915:
908:
1033:
Organoborane activation with hydroxide or alkoxide and treatment with X
895:
880:
850:
807:
426:
419:
2480:
Lachance, H.; Hall, D. (2008). "Allylboration of Carbonyl Compounds".
1989:
1683:
905:α-Haloester enolates add similarly to boranes, but with lower yields:
2818:
1177:
1100:
939:
711:
688:
474:
411:
380:
332:
109:
70:
62:
1184:
819:
664:
K, precursors to nucleophilic alkyl and aryl boron difluorides, ArBF
2386:
Brown, H. C.; Rogic M. M.; Nambu H.; Rathke, M. W.
1252:
818:
631:
450:) are boryl complexes, corresponding to the notional boryl anion R
288:
180:
The most-studied class of organoboron compounds has the formula BR
171:
58:
29:
1092:
1080:
152:
2790:
2366:
Midland, M. M.; Zolopa, A. R.; Halterman, R. L.
804:
alkenylboranes, as in the first step of this olefin synthesis:
590:
Each boron atom has an attached proton and is coordinated to a
299:
backbone. 9-BBN is more reactive towards alkenes than alkynes.
2020:
October 1, 2007 Volume 85, Number 40 p. 10
594:. The parent structure with the additional carbene ligands is
2734:"Boron delivery agents for neutron capture therapy of cancer"
1279:, which relies on boron coordination to the carbonyl oxygen.
1925:
Curran, D. P.; Solovyev, A.; Makhlouf, Brahmi M.;
1323:
1304:
1294:
1054:
1043:
989:
975:
914:
907:
894:
879:
849:
806:
787:
670:
582:
494:
139:, such as the triorganoboranes. These compounds are strong
2357:, J. H. Bewster, Ed., Plenum, 1978, p. 229.
1356:
Organoboron compounds have long been discussed for use as
2732:
Barth, Rolf F.; Mi, Peng; Yang, Weilian (December 2018).
2607:
Brown, H. C.; Rathke, M. W.; Rogic, M. M.
1230:
1212:
1161:
1143:
1125:
1484:) and the x-ray crystal structures of 2 (Mes = 2,4,6,-Me
1025:
Oxidation of an alkenylborane gives an boron-free enol.
1530:
John Wiley & Sons, Inc. New York: 1975.
522:, can be detected at low temperature. The derivative CH
473:
BH. Instead these reactions afford the octet-complete
235:. It is obtained by hydroboration of (â)âαâpinene with
176:
Structure of a rare monomeric boron hydride, R = i-Pr.
1113:
1041:
permits only halogenation of the hydroborated olefin:
758:
via a transition-metal catalyst. A common reagent is
2715:
Negishi E.-I.; Abramovitch, A.; Merrill, R. E.
3455:
2518:Angewandte Chemie International Edition in English
1236:
823:Overall synthetic routes via organoboron compounds
580:are rare. One example is the diborene (RHB=BHR):
2355:Aspects of Mechanism and Organometallic Chemistry
27:Study of compounds containing a boron-carbon bond
2162:Molander, Gary A.; Canturk, Belgin (2009).
858:likely to migrate upon nucleophilic activation.
1237:{\displaystyle {\ce {R1-BY2{}+R2-X->R1-R2}}}
283:BH exhibits improved thermal stability than Sia
1577:Encyclopedia of Reagents for Organic Synthesis
2802:
773:reacts with alkylboranes to form an unstable
560:adducts can be synthesised directly from the
8:
2406:Nesmeyanov, A. N.; Sokolik, R. A.
1383:. Oxford Chemistry Primers No. 1; 1991.
800:Alkynylboranes attack electrophiles to give
192:boron center that is typically only weakly
143:, but typically too sterically hindered to
2809:
2795:
2787:
2459:Pasto, D. J.; Wojtkowski, P. W.
2337:Miyaura M.; Sasaki N.; Itoh M.; Suzuki A.
1779:(3rd ed.). New York: Academic Press.
200:itself. Trisubstituted derivatives, e.g.
2821:with other elements in the periodic table
2767:
2749:
2664:
2188:
1909:
1229:
1224:
1215:
1211:
1206:
1188:
1186:
1178:
1172:
1164:
1160:
1155:
1146:
1142:
1137:
1128:
1124:
1119:
1114:
1112:
2211:Carey, F. A.; Sundberg, R. J.
1342:was used to ignite the JP-7 fuel of the
303:Borinic and boronic acids and esters (BR
2587:Midland, M. M.; Brown, H. C.
2085:Angewandte Chemie International Edition
2035:Angewandte Chemie International Edition
1931:Angewandte Chemie International Edition
1637:Angewandte Chemie International Edition
1393:
695:stereochemistry. Hydroboration occurs
335:(n = 0). Boronic acids are key to the
80:Organoboranes and -borates enable many
2838:
2583:
2581:
2313:
2311:
2274:Corey, E. J.; Ravindranathan, T.
2251:Rathke, M. W.; Brown, H. C.
1400:
2270:
2268:
1438:Negishi E.-I.; Idacavage, M. J.
1004:hydroboration-oxidation reaction pair
634:) and the ethyl or pentafluorophenyl
367:; the best known is orthocarborane, C
7:
3480:Academic research, no widespread use
2627:Negishi, E.-i.; Lew, G.; Yoshida T.
1434:
1432:
965:) is the first step in a two-carbon
827:The key property of organoboranes (R
223:), produced by the hydroboration of
2122:from the original on July 22, 2018.
1610:Journal of Organometallic Chemistry
835:B, generated via addition of R to R
691:insert into borane B-H bonds, with
391:Bora-substituted aromatic compounds
2231:Jacob III, P.; Brown, H. C.
1185:
155:groups can lend the C-B bond some
25:
2410:, North-Holland, Amsterdam, 1967.
1362:neutron capture therapy of cancer
946:, and can then be converted to a
295:BH, perhaps because of it rigid C
287:BH. A versatile dialkylborane is
3372:
3291:
3223:
3128:
2828:
1970:Schaefer III, Henry F.
702:â on the same alkene face. The
642:addition will effect a borate (R
163:Classes of organoboron compounds
2017:Chemical & Engineering News
1879:Chemical & Engineering News
605:is based on similar chemistry.
534:is fairly stable, but prone to
124:The C-B bond has low polarity (
77:), as in the trialkyl boranes.
1974:v. R. Schleyer, Paul
1882:2006; Volume 84 (41): 11
1381:The Roles of Boron and Silicon
873:Organoboranes are unstable to
351:Boron is renowned for cluster
1:
2294:Allred, A. L.; Rochow, E. G.
1719:10.1016/S0040-4039(00)81675-5
1622:10.1016/S0022-328X(00)81001-3
1585:10.1002/047084289X.rd248.pub3
1528:Organic Syntheses via Boranes
720:Hydroboration with borane (BH
717:and the empty boron orbital.
618:Simple organoboranes such as
510:(RB=CRR) with a boronâcarbon
96:. Most reactions transfer a
2695:Rathke, M. W.; Brown, H. C.
1735:Journal of Organic Chemistry
1283:Other synthetic applications
1063:Transmetalation and coupling
777:. Then an alkyl substituent
728:consume the remainder. The
624:tris(pentafluorophenyl)boron
518:. The parent compound, HB=CH
446:with metal-boron bonds (MâBR
133:electron-deficient compounds
2492:10.1002/0471264180.or073.01
2486:. Vol. 73. p. 1.
2439:Hooz, J.; Gunn, D. M.
2012:Neutral Diborene Is A First
1775:Grimes, R. N. (2016).
1457:10.1002/0471264180.or033.01
1067:Organoboron compounds also
566:lithium triethylborohydride
3523:
2213:Advanced Organic Chemistry
1411:Elschenbroich, Christoph.
1006:oxidizes the borane to an
766:From other boron compounds
743:
514:are rare. One example is
436:
168:Organoboranes and hydrides
147:. Electron donation from
120:Properties of the B-C bond
3369:
3288:
2840:
2836:
2826:
2751:10.1186/s40880-018-0299-7
888:Addition to halocarbonyls
363:with carbon vertices are
1351:Lockheed SR-71 Blackbird
1251:Borane hydrides such as
549:and boranes form stable
454:B. Related ligands are
444:Organometallic compounds
315:Compounds of the type BR
100:boron substituent to an
82:chemical transformations
2564:10.1351/pac200274010043
1844:10.1126/science.1131914
1760:Dhillon, R. S. (2007).
1344:Pratt & Whitney J58
490:N-heterocyclic carbenes
237:borane dimethyl sulfide
3475:Many uses in chemistry
3470:Core organic chemistry
2181:10.1002/anie.200904306
2097:10.1002/anie.201610072
2047:10.1002/anie.201208189
1943:10.1002/anie.201102717
1911:10.1002/zaac.200300396
1379:Thomas, Susan E.
1347:variable cycle engines
1328:
1309:
1299:
1238:
1200:
1071:easily, especially to
1059:
1048:
994:
980:
919:
912:
899:
884:
854:
824:
811:
792:
760:bis(pinacolato)diboron
675:
614:From Grignard reagents
587:
499:
243:organozinc compounds.
177:
65:; typically, they are
43:organoborane chemistry
35:
3507:Organoboron compounds
2738:Cancer Communications
2319:J. Organometal. Chem.
2296:J. Inorg. Nucl. Chem.
2169:Angew. Chem. Int. Ed.
1799:Hall, Dennis G.
1426:â Wiley-VCH, Weinheim
1358:boron delivery agents
1327:
1319:reductively eliminate
1317:Organoborates anions
1308:
1298:
1239:
1173:
1058:
1047:
993:
979:
930:In allylboration, an
926:Addition to carbonyls
918:
911:
898:
883:
853:
822:
810:
791:
674:
662:trifluoroborate salts
626:can be prepared from
586:
498:
175:
47:organoboron compounds
39:Organoboron chemistry
33:
18:Organoborane compound
2031:Braunschweig, Holger
1898:Z. Anorg. Allg. Chem
1562:10.1055/s-1974-23248
1472:(Trip - 2,4,6-iso-Pr
1111:
1105:palladium(0) complex
875:BrĂžnstedâLowry acids
658:potassium bifluoride
542:NHC adducts of boron
425:The cyclic compound
410:The cyclic compound
102:electrophilic center
88:â most importantly,
2675:10.1021/cr00039a007
2149:10.1021/jo00115a016
1984:(41): 12412â12413.
1966:King, R. Bruce
1937:(44): 10294â10317.
1872:Halford, Bethany. "
1836:2006Sci...314..113S
1747:10.1021/jo00036a008
1707:Tetrahedron Letters
1514:10.1021/om00115a023
1269:asymmetric catalyst
1232:
1214:
1199:
1183:
1163:
1145:
1127:
225:tetramethylethylene
1526:Brown, H. C.
1329:
1310:
1300:
1275:reductions is the
1263:)borohydride) are
1234:
1220:
1202:
1196:
1151:
1133:
1115:
1075:compounds. In the
1060:
1049:
995:
981:
920:
913:
900:
885:
855:
825:
812:
793:
783:sodium borohydride
708:concerted reaction
697:stereospecifically
676:
588:
500:
178:
131:Boron often forms
108:. In particular,
55:chemical compounds
36:
3494:
3493:
3450:
3449:
2697:J. Am. Chem. Soc.
2609:J. Am. Chem. Soc.
2483:Organic Reactions
2441:J. Am. Chem. Soc.
2421:J. Am. Chem. Soc.
2388:J. Am. Chem. Soc.
2368:J. Am. Chem. Soc.
2339:Tetrahedron Lett.
2276:J. Am. Chem. Soc.
2253:J. Am. Chem. Soc.
2175:(49): 9240â9261.
2143:(10): 3020â3027.
2041:(13): 3574â3583.
1990:10.1021/ja075932i
1830:(5796): 113â115.
1684:10.1021/ol0068400
1643:(13): 2294â2297.
1579:. pp. 1â10.
1223:
1205:
1198:
1195:
1192:
1189:
1181:
1171:
1154:
1136:
1118:
1012:hydrogen peroxide
831:B) and borates (R
536:cyclodimerisation
508:Alkylideneboranes
503:Alkylideneboranes
416:structural analog
385:cyclopentadienide
361:cluster compounds
274:, abbreviated Sia
215:. One example is
126:electronegativity
104:either inter- or
86:organic chemistry
16:(Redirected from
3514:
3486:
3481:
3476:
3471:
3376:
3375:
3295:
3294:
3227:
3226:
3132:
3131:
2829:
2811:
2804:
2797:
2788:
2782:
2781:
2771:
2753:
2729:
2723:
2713:
2707:
2693:
2687:
2686:
2668:
2659:(7): 2457â2483.
2653:Chemical Reviews
2641:
2635:
2625:
2619:
2605:
2599:
2585:
2576:
2575:
2549:
2540:
2534:
2533:
2512:
2506:
2505:
2477:
2471:
2457:
2451:
2437:
2431:
2417:
2411:
2404:
2398:
2384:
2378:
2364:
2358:
2351:
2345:
2335:
2329:
2315:
2306:
2292:
2286:
2272:
2263:
2249:
2243:
2229:
2223:
2209:
2203:
2202:
2192:
2159:
2153:
2152:
2130:
2124:
2123:
2121:
2082:
2073:
2067:
2066:
2027:
2021:
2008:
2002:
2001:
1978:J. Am. Chem. Soc
1961:
1955:
1954:
1922:
1916:
1915:
1913:
1889:
1883:
1870:
1864:
1863:
1817:
1811:
1797:
1791:
1790:
1772:
1766:
1765:
1757:
1751:
1750:
1729:
1723:
1722:
1702:
1696:
1695:
1667:
1661:
1660:
1632:
1626:
1625:
1605:
1599:
1598:
1572:
1566:
1565:
1545:
1539:
1524:
1518:
1517:
1465:
1459:
1436:
1427:
1409:
1403:
1398:
1384:
1243:
1241:
1240:
1235:
1233:
1231:
1228:
1221:
1219:
1213:
1210:
1203:
1201:
1197:
1193:
1190:
1187:
1182:
1179:
1169:
1168:
1162:
1159:
1152:
1147:
1144:
1141:
1134:
1132:
1126:
1123:
1116:
750:Metal-catalyzed
704:transition state
693:anti-Markovnikov
636:Grignard reagent
562:imidazolium salt
341:Trimethyl borate
231:, it is a dimer
204:, are monomers.
106:intramolecularly
21:
3522:
3521:
3517:
3516:
3515:
3513:
3512:
3511:
3497:
3496:
3495:
3490:
3489:
3484:
3479:
3474:
3469:
3451:
3373:
3292:
3224:
3129:
2822:
2815:
2785:
2731:
2730:
2726:
2714:
2710:
2694:
2690:
2666:10.1.1.735.7660
2643:
2642:
2638:
2626:
2622:
2606:
2602:
2586:
2579:
2552:Pure Appl. Chem
2547:
2542:
2541:
2537:
2514:
2513:
2509:
2502:
2479:
2478:
2474:
2458:
2454:
2438:
2434:
2418:
2414:
2405:
2401:
2385:
2381:
2365:
2361:
2353:Zweifel, G. in
2352:
2348:
2336:
2332:
2316:
2309:
2293:
2289:
2273:
2266:
2250:
2246:
2230:
2226:
2210:
2206:
2161:
2160:
2156:
2132:
2131:
2127:
2119:
2080:
2075:
2074:
2070:
2029:
2028:
2024:
2009:
2005:
1963:
1962:
1958:
1927:Fensterbank, L.
1924:
1923:
1919:
1891:
1890:
1886:
1871:
1867:
1819:
1818:
1814:
1798:
1794:
1787:
1774:
1773:
1769:
1759:
1758:
1754:
1731:
1730:
1726:
1704:
1703:
1699:
1672:Organic Letters
1669:
1668:
1664:
1634:
1633:
1629:
1607:
1606:
1602:
1595:
1574:
1573:
1569:
1547:
1546:
1542:
1525:
1521:
1502:Organometallics
1499:
1495:
1491:
1487:
1483:
1479:
1475:
1471:
1467:
1466:
1462:
1437:
1430:
1413:Organometallics
1410:
1406:
1399:
1395:
1391:
1378:
1375:
1373:Further reading
1370:
1334:
1315:
1313:Carbonyl groups
1290:
1285:
1265:reducing agents
1249:
1247:Reducing agents
1109:
1108:
1077:Suzuki reaction
1073:organopalladium
1065:
1036:
1031:
1000:
934:adds across an
928:
890:
871:
838:
834:
830:
817:
798:
775:borane carbonyl
771:Carbon monoxide
768:
748:
742:
723:
681:
667:
655:
645:
628:trifluoroborane
616:
611:
574:
544:
533:
529:
525:
521:
505:
480:
472:
453:
449:
441:
435:
433:Boryl compounds
406:
402:
393:
378:
374:
370:
349:
337:Suzuki reaction
322:
318:
313:
310:
306:
298:
294:
286:
282:
277:
269:
265:
261:
257:
253:
249:
234:
230:
222:
214:
190:trigonal-planar
187:
183:
170:
165:
135:without a full
122:
76:
69:derivatives of
28:
23:
22:
15:
12:
11:
5:
3520:
3518:
3510:
3509:
3499:
3498:
3492:
3491:
3488:
3487:
3482:
3477:
3472:
3467:
3464:Chemical bonds
3460:
3459:
3457:
3453:
3452:
3448:
3447:
3442:
3437:
3432:
3427:
3422:
3417:
3412:
3407:
3402:
3397:
3392:
3387:
3382:
3377:
3370:
3367:
3366:
3361:
3356:
3351:
3346:
3341:
3336:
3331:
3326:
3321:
3316:
3311:
3306:
3301:
3296:
3289:
3286:
3285:
3281:
3280:
3277:
3274:
3271:
3268:
3265:
3262:
3259:
3256:
3253:
3250:
3247:
3244:
3239:
3236:
3233:
3228:
3221:
3216:
3212:
3211:
3208:
3203:
3198:
3193:
3188:
3183:
3178:
3173:
3168:
3163:
3158:
3153:
3148:
3143:
3138:
3133:
3126:
3121:
3115:
3114:
3109:
3104:
3099:
3094:
3089:
3084:
3079:
3074:
3069:
3064:
3059:
3054:
3049:
3044:
3039:
3034:
3032:
3027:
3021:
3020:
3015:
3010:
3005:
3000:
2995:
2990:
2985:
2980:
2975:
2970:
2965:
2960:
2955:
2950:
2945:
2940:
2938:
2933:
2927:
2926:
2921:
2916:
2911:
2906:
2901:
2896:
2891:
2885:
2884:
2881:
2876:
2871:
2866:
2861:
2856:
2851:
2845:
2844:
2841:
2839:
2837:
2835:
2827:
2824:
2823:
2816:
2814:
2813:
2806:
2799:
2791:
2784:
2783:
2724:
2708:
2688:
2636:
2620:
2600:
2577:
2535:
2524:(1â2): 81â84.
2507:
2501:978-0471264187
2500:
2472:
2452:
2432:
2412:
2399:
2379:
2359:
2346:
2330:
2317:Negishi E.-I.
2307:
2287:
2264:
2244:
2224:
2204:
2154:
2125:
2068:
2022:
2010:Dagani, Ron. "
2003:
1956:
1917:
1904:(4): 508â518.
1884:
1865:
1812:
1792:
1785:
1767:
1752:
1724:
1697:
1662:
1627:
1600:
1593:
1567:
1540:
1519:
1497:
1493:
1489:
1485:
1481:
1477:
1473:
1469:
1460:
1428:
1404:
1392:
1390:
1387:
1386:
1385:
1374:
1371:
1369:
1366:
1340:Triethylborane
1333:
1330:
1314:
1311:
1289:
1286:
1284:
1281:
1248:
1245:
1227:
1218:
1209:
1176:
1167:
1158:
1150:
1140:
1131:
1122:
1091:couples to an
1064:
1061:
1039:disiamylborane
1034:
1030:
1027:
1020:chromium oxide
999:
996:
927:
924:
889:
886:
870:
867:
836:
832:
828:
816:
813:
797:
796:Alkenylboranes
794:
767:
764:
744:Main article:
741:
738:
730:chelate effect
721:
680:
677:
665:
653:
643:
620:triethylborane
615:
612:
610:
607:
573:
570:
558:Triethylborane
543:
540:
531:
527:
523:
519:
504:
501:
478:
470:
458:(MâB(R)âM).
451:
447:
437:Main article:
434:
431:
404:
400:
392:
389:
376:
372:
368:
348:
347:Boron clusters
345:
329:boronic esters
325:borinic esters
320:
316:
312:
308:
304:
301:
296:
292:
284:
280:
275:
272:disiamylborane
267:
263:
259:
255:
251:
247:
232:
228:
220:
212:
185:
181:
169:
166:
164:
161:
121:
118:
74:
49:, also called
26:
24:
14:
13:
10:
9:
6:
4:
3:
2:
3519:
3508:
3505:
3504:
3502:
3483:
3478:
3473:
3468:
3465:
3462:
3461:
3458:
3454:
3446:
3443:
3441:
3438:
3436:
3433:
3431:
3428:
3426:
3423:
3421:
3418:
3416:
3413:
3411:
3408:
3406:
3403:
3401:
3398:
3396:
3393:
3391:
3388:
3386:
3383:
3381:
3378:
3371:
3368:
3365:
3362:
3360:
3357:
3355:
3352:
3350:
3347:
3345:
3342:
3340:
3337:
3335:
3332:
3330:
3327:
3325:
3322:
3320:
3317:
3315:
3312:
3310:
3307:
3305:
3302:
3300:
3297:
3290:
3287:
3283:
3282:
3278:
3275:
3272:
3269:
3266:
3263:
3260:
3257:
3254:
3251:
3248:
3245:
3243:
3240:
3237:
3234:
3232:
3229:
3222:
3220:
3217:
3214:
3213:
3209:
3207:
3204:
3202:
3199:
3197:
3194:
3192:
3189:
3187:
3184:
3182:
3179:
3177:
3174:
3172:
3169:
3167:
3164:
3162:
3159:
3157:
3154:
3152:
3149:
3147:
3144:
3142:
3139:
3137:
3134:
3127:
3125:
3122:
3120:
3117:
3116:
3113:
3110:
3108:
3105:
3103:
3100:
3098:
3095:
3093:
3090:
3088:
3085:
3083:
3080:
3078:
3075:
3073:
3070:
3068:
3065:
3063:
3060:
3058:
3055:
3053:
3050:
3048:
3045:
3043:
3040:
3038:
3035:
3033:
3031:
3028:
3026:
3023:
3022:
3019:
3016:
3014:
3011:
3009:
3006:
3004:
3001:
2999:
2996:
2994:
2991:
2989:
2986:
2984:
2981:
2979:
2976:
2974:
2971:
2969:
2966:
2964:
2961:
2959:
2956:
2954:
2951:
2949:
2946:
2944:
2941:
2939:
2937:
2934:
2932:
2929:
2928:
2925:
2922:
2920:
2917:
2915:
2912:
2910:
2907:
2905:
2902:
2900:
2897:
2895:
2892:
2890:
2887:
2886:
2882:
2880:
2877:
2875:
2872:
2870:
2867:
2865:
2862:
2860:
2857:
2855:
2852:
2850:
2847:
2846:
2842:
2834:
2831:
2830:
2825:
2820:
2817:Compounds of
2812:
2807:
2805:
2800:
2798:
2793:
2792:
2789:
2779:
2775:
2770:
2765:
2761:
2757:
2752:
2747:
2743:
2739:
2735:
2728:
2725:
2721:
2718:
2717:Chem. Commun.
2712:
2709:
2705:
2701:
2698:
2692:
2689:
2684:
2680:
2676:
2672:
2667:
2662:
2658:
2654:
2650:
2646:
2645:Miyaura Norio
2640:
2637:
2633:
2630:
2629:Chem. Commun.
2624:
2621:
2617:
2613:
2610:
2604:
2601:
2597:
2593:
2590:
2589:J. Org. Chem.
2584:
2582:
2578:
2573:
2569:
2565:
2561:
2557:
2553:
2546:
2539:
2536:
2531:
2527:
2523:
2519:
2511:
2508:
2503:
2497:
2493:
2489:
2485:
2484:
2476:
2473:
2469:
2465:
2462:
2461:J. Org. Chem.
2456:
2453:
2449:
2445:
2442:
2436:
2433:
2429:
2425:
2422:
2416:
2413:
2409:
2403:
2400:
2396:
2392:
2389:
2383:
2380:
2376:
2372:
2369:
2363:
2360:
2356:
2350:
2347:
2343:
2340:
2334:
2331:
2327:
2323:
2320:
2314:
2312:
2308:
2304:
2300:
2297:
2291:
2288:
2284:
2280:
2277:
2271:
2269:
2265:
2261:
2257:
2254:
2248:
2245:
2241:
2237:
2234:
2233:J. Org. Chem.
2228:
2225:
2222:
2221:0-306-41088-5
2218:
2214:
2208:
2205:
2200:
2196:
2191:
2186:
2182:
2178:
2174:
2171:
2170:
2165:
2158:
2155:
2150:
2146:
2142:
2139:
2138:
2137:J. Org. Chem.
2129:
2126:
2118:
2114:
2110:
2106:
2102:
2098:
2094:
2091:(1): 96â115.
2090:
2086:
2079:
2072:
2069:
2064:
2060:
2056:
2052:
2048:
2044:
2040:
2036:
2032:
2026:
2023:
2019:
2018:
2013:
2007:
2004:
1999:
1995:
1991:
1987:
1983:
1979:
1975:
1971:
1967:
1960:
1957:
1952:
1948:
1944:
1940:
1936:
1932:
1928:
1921:
1918:
1912:
1907:
1903:
1899:
1895:
1888:
1885:
1881:
1880:
1875:
1869:
1866:
1861:
1857:
1853:
1849:
1845:
1841:
1837:
1833:
1829:
1825:
1824:
1816:
1813:
1810:
1809:3-527-30991-8
1806:
1802:
1796:
1793:
1788:
1786:9780128019054
1782:
1778:
1771:
1768:
1763:
1756:
1753:
1748:
1744:
1740:
1736:
1728:
1725:
1720:
1716:
1712:
1708:
1701:
1698:
1693:
1689:
1685:
1681:
1678:(1): 127â30.
1677:
1673:
1666:
1663:
1658:
1654:
1650:
1646:
1642:
1638:
1631:
1628:
1623:
1619:
1615:
1611:
1604:
1601:
1596:
1594:9780470842898
1590:
1586:
1582:
1578:
1571:
1568:
1563:
1559:
1555:
1551:
1544:
1541:
1537:
1536:0-471-11280-1
1533:
1529:
1523:
1520:
1515:
1511:
1507:
1503:
1464:
1461:
1458:
1454:
1450:
1446:
1443:
1442:
1435:
1433:
1429:
1425:
1424:3-527-29390-6
1421:
1418:
1415:3rd Ed.
1414:
1408:
1405:
1402:
1397:
1394:
1388:
1382:
1377:
1376:
1372:
1367:
1365:
1363:
1359:
1354:
1352:
1349:powering the
1348:
1345:
1341:
1337:
1331:
1326:
1322:
1320:
1312:
1307:
1303:
1297:
1293:
1287:
1282:
1280:
1278:
1274:
1270:
1266:
1262:
1259:(lithium tri(
1258:
1254:
1246:
1244:
1225:
1216:
1207:
1174:
1165:
1156:
1148:
1138:
1129:
1120:
1106:
1102:
1098:
1094:
1090:
1086:
1082:
1078:
1074:
1070:
1069:transmetalate
1062:
1057:
1053:
1046:
1042:
1040:
1028:
1026:
1023:
1021:
1017:
1013:
1009:
1005:
997:
992:
988:
986:
978:
974:
972:
968:
964:
960:
956:
952:
949:
945:
944:allylic shift
941:
937:
933:
925:
923:
917:
910:
906:
903:
897:
893:
887:
882:
878:
876:
868:
866:
864:
863:sp-hybridized
859:
852:
848:
846:
841:
821:
814:
809:
805:
803:
795:
790:
786:
784:
780:
776:
772:
765:
763:
761:
757:
753:
747:
740:By borylation
739:
737:
735:
731:
727:
718:
716:
713:
709:
705:
701:
698:
694:
690:
686:
685:hydroboration
678:
673:
669:
663:
659:
651:
650:Boronic acids
647:
641:
637:
633:
629:
625:
621:
613:
608:
606:
604:
599:
597:
593:
585:
581:
579:
571:
569:
567:
563:
559:
555:
552:
548:
541:
539:
537:
517:
513:
509:
502:
497:
493:
491:
487:
486:isoelectronic
482:
476:
468:
464:
459:
457:
445:
440:
432:
430:
429:is aromatic.
428:
423:
421:
417:
413:
408:
398:
390:
388:
386:
383:similarly to
382:
366:
362:
358:
354:
346:
344:
342:
338:
334:
331:(n = 1), and
330:
326:
302:
300:
290:
273:
244:
240:
238:
226:
218:
210:
205:
203:
202:triethylboron
199:
195:
191:
174:
167:
162:
160:
158:
154:
150:
146:
142:
141:electrophiles
138:
134:
129:
127:
119:
117:
115:
111:
107:
103:
99:
95:
94:carboboration
91:
90:hydroboration
87:
83:
78:
72:
68:
64:
60:
56:
52:
51:organoboranes
48:
44:
40:
32:
19:
3485:Bond unknown
2858:
2741:
2737:
2727:
2719:
2716:
2711:
2703:
2699:
2696:
2691:
2656:
2652:
2649:Suzuki Akira
2639:
2631:
2628:
2623:
2615:
2611:
2608:
2603:
2595:
2591:
2588:
2558:(1): 43â55.
2555:
2551:
2538:
2521:
2517:
2510:
2481:
2475:
2467:
2463:
2460:
2455:
2447:
2443:
2440:
2435:
2427:
2423:
2420:
2415:
2407:
2402:
2394:
2390:
2387:
2382:
2374:
2370:
2367:
2362:
2354:
2349:
2341:
2338:
2333:
2325:
2321:
2318:
2302:
2298:
2295:
2290:
2282:
2278:
2275:
2259:
2255:
2252:
2247:
2239:
2235:
2232:
2227:
2212:
2207:
2172:
2167:
2157:
2140:
2135:
2128:
2088:
2084:
2071:
2038:
2034:
2025:
2015:
2006:
1981:
1977:
1959:
1934:
1930:
1920:
1901:
1897:
1887:
1877:
1868:
1827:
1821:
1815:
1800:
1795:
1776:
1770:
1761:
1755:
1741:(10): 2794.
1738:
1734:
1727:
1713:(13): 1433.
1710:
1706:
1700:
1675:
1671:
1665:
1640:
1636:
1630:
1613:
1609:
1603:
1576:
1570:
1556:(2): 77â89.
1553:
1549:
1543:
1527:
1522:
1505:
1501:
1496:) and HBtrip
1463:
1448:
1444:
1439:
1416:
1412:
1407:
1396:
1380:
1355:
1338:
1335:
1332:Applications
1316:
1301:
1291:
1277:CBS catalyst
1257:L-selectride
1250:
1089:boronic acid
1066:
1050:
1032:
1029:Halogenation
1024:
1001:
982:
967:homologation
963:alpha-pinene
929:
921:
904:
901:
891:
872:
869:Protonolysis
860:
856:
845:1,2-migrates
842:
826:
801:
799:
769:
749:
719:
699:
682:
679:From alkenes
648:
617:
600:
589:
578:double bonds
576:Boron-boron
575:
553:
550:
545:
507:
506:
483:
460:
442:
424:
409:
407:B-pyridine.
394:
357:dodecaborate
350:
314:
245:
241:
217:thexylborane
209:redistribute
206:
194:Lewis acidic
179:
130:
123:
114:protonolysis
98:nucleophilic
79:
50:
46:
42:
38:
37:
1764:. Springer.
1508:: 146â150.
1441:Org. React.
1401:Thomas 1991
1018:group with
998:Oxygenation
959:epothilones
948:homoallylic
932:allylborane
756:sigma bonds
656:react with
601:A reported
596:diborane(2)
592:NHC carbene
516:borabenzene
512:double bond
481:HB-base.
467:deprotonate
397:borabenzene
323:are called
159:character.
157:double bond
34:Organoboron
1777:Carboranes
1368:References
1103:through a
971:acetogenin
752:borylation
746:Borylation
726:byproducts
715:p-orbitals
660:K to form
638:. Further
551:NHC-borane
484:Compounds
439:borylation
365:carboranes
3466:to carbon
2760:2523-3548
2744:(1): 35.
2661:CiteSeerX
2105:1521-3773
2055:1521-3773
1550:Synthesis
1389:Footnotes
1261:sec-butyl
1217:−
1166:−
1130:−
1107:catalyst:
985:aldehydes
815:Reactions
706:for this
640:carbanion
609:Synthesis
572:Diborenes
488:with the
469:boranes R
456:borylenes
327:(n = 2),
53:. These
3501:Category
2778:29914561
2683:53050782
2572:49223984
2199:19899086
2117:Archived
2113:27860056
2063:23362015
1998:17887683
1951:21898724
1860:21040230
1852:17023656
1692:11429854
1657:10941068
1288:Alcohols
1273:carbonyl
1194:catalyst
1175:→
1016:carbonyl
1014:or to a
942:with an
936:aldehyde
779:migrates
603:diboryne
526:B=C(SiMe
198:diborane
145:dimerize
57:combine
45:studies
3284:
2769:6006782
2706:, 2740.
2618:, 5038.
2598:, 2845.
2470:, 1790.
2450:, 6195.
2397:, 2147.
2285:, 4013.
2262:, 2740.
2190:2917751
1832:Bibcode
1823:Science
1616:: 299.
1008:alcohol
953:during
951:alcohol
689:alkenes
554:adducts
465:do not
461:Strong
427:borepin
420:pyrrole
355:, e.g.
353:species
333:borates
67:organic
3456:Legend
2819:carbon
2776:
2766:
2758:
2722:, 138.
2681:
2663:
2634:, 874.
2570:
2498:
2430:, 818.
2377:, 248.
2344:, 173.
2328:, 281.
2305:, 264.
2242:, 579.
2219:
2197:
2187:
2111:
2103:
2061:
2053:
1996:
1949:
1858:
1850:
1807:
1783:
1690:
1655:
1591:
1534:
1422:
1101:halide
955:workup
940:ketone
712:olefin
652:RB(OH)
475:adduct
412:borole
381:ligate
219:(ThxBH
71:borane
63:carbon
2679:S2CID
2568:S2CID
2548:(PDF)
2120:(PDF)
2081:(PDF)
1856:S2CID
1451:, 1.
1267:. An
1253:9-BBN
1097:vinyl
1095:- or
1085:vinyl
1083:- or
1079:, an
1010:with
802:trans
734:9-BBN
632:ether
463:bases
289:9-BBN
149:vinyl
137:octet
59:boron
2774:PMID
2756:ISSN
2720:1975
2700:1967
2632:1973
2612:1968
2592:1975
2496:ISBN
2464:1971
2444:1969
2424:1968
2391:1969
2371:1979
2342:1977
2322:1976
2299:1958
2279:1972
2256:1967
2236:1977
2217:ISBN
2195:PMID
2109:PMID
2101:ISSN
2059:PMID
2051:ISSN
1994:PMID
1947:PMID
1848:PMID
1805:ISBN
1781:ISBN
1688:PMID
1653:PMID
1589:ISBN
1554:1974
1532:ISBN
1445:1985
1420:ISBN
1417:2006
1271:for
1255:and
1180:Base
1093:aryl
1081:aryl
1002:The
646:B).
630:(in
564:and
547:NHCs
414:, a
339:.
319:(OR)
307:(OR)
153:aryl
151:and
92:and
61:and
3430:CEs
3425:CCf
3420:CBk
3415:CCm
3410:CAm
3405:CPu
3400:CNp
3390:CPa
3385:CTh
3364:CYb
3359:CTm
3354:CEr
3349:CHo
3344:CDy
3339:CTb
3334:CGd
3329:CEu
3324:CSm
3319:CPm
3314:CNd
3309:CPr
3304:CCe
3299:CLa
3279:Og
3276:Ts
3273:Lv
3270:Mc
3267:Fl
3264:Nh
3261:Cn
3258:Rg
3255:Ds
3252:Mt
3249:Hs
3246:Bh
3242:CSg
3238:Db
3235:Rf
3219:CRa
3215:Fr
3210:Rn
3206:CAt
3201:CPo
3196:CBi
3191:CPb
3186:CTl
3181:CHg
3176:CAu
3171:CPt
3166:CIr
3161:COs
3156:CRe
3146:CTa
3141:CHf
3136:CLu
3124:CBa
3119:CCs
3112:CXe
3102:CTe
3097:CSb
3092:CSn
3087:CIn
3082:CCd
3077:CAg
3072:CPd
3067:CRh
3062:CRu
3057:CTc
3052:CMo
3047:CNb
3042:CZr
3030:CSr
3025:CRb
3018:CKr
3013:CBr
3008:CSe
3003:CAs
2998:CGe
2993:CGa
2988:CZn
2983:CCu
2978:CNi
2973:CCo
2968:CFe
2963:CMn
2958:CCr
2948:CTi
2943:CSc
2936:CCa
2924:CAr
2919:CCl
2904:CSi
2899:CAl
2894:CMg
2889:CNa
2883:Ne
2854:CBe
2849:CLi
2843:He
2764:PMC
2746:doi
2671:doi
2560:doi
2526:doi
2488:doi
2375:101
2326:108
2185:PMC
2177:doi
2145:doi
2093:doi
2043:doi
1986:doi
1982:129
1939:doi
1906:doi
1902:630
1876:"
1840:doi
1828:314
1743:doi
1715:doi
1680:doi
1645:doi
1618:doi
1614:218
1581:doi
1558:doi
1510:doi
1500:".
1453:doi
1360:in
969:to
938:or
785:):
700:syn
683:In
622:or
418:of
395:In
321:3-n
309:3-n
279:Chx
186:3ân
110:α,ÎČ
84:in
73:(BH
41:or
3503::
3445:No
3440:Md
3435:Fm
3395:CU
3380:Ac
3231:Lr
3151:CW
3107:CI
3037:CY
2953:CV
2931:CK
2914:CS
2909:CP
2879:CF
2874:CO
2869:CN
2864:CC
2859:CB
2833:CH
2772:.
2762:.
2754:.
2742:38
2740:.
2736:.
2704:89
2702:,
2677:.
2669:.
2657:95
2655:.
2647:;
2616:90
2614:,
2596:40
2594:,
2580:^
2566:.
2556:74
2554:.
2550:.
2522:37
2520:.
2494:.
2468:36
2466:,
2448:91
2446:,
2428:90
2426:,
2395:91
2393:,
2373:,
2324:,
2310:^
2301:,
2283:94
2281:,
2267:^
2260:89
2258:,
2240:42
2238:,
2215:.
2193:.
2183:.
2173:48
2166:.
2141:60
2115:.
2107:.
2099:.
2089:56
2087:.
2083:.
2057:.
2049:.
2039:52
2037:.
2014:"
1992:.
1980:.
1972:;
1968:;
1945:.
1935:50
1933:.
1900:.
1896:.
1854:.
1846:.
1838:.
1826:.
1803:.
1739:57
1737:.
1711:24
1709:.
1686:.
1674:.
1651:.
1641:39
1639:.
1612:.
1587:.
1552:.
1504:.
1449:33
1447:,
1431:^
1364:.
1353:.
1191:Pd
1135:BY
1022:.
987::
973::
762:.
736:.
687:,
668::
598:.
568:.
556:.
538:.
387:.
377:12
373:10
254:Me
239:.
2810:e
2803:t
2796:v
2780:.
2748::
2685:.
2673::
2574:.
2562::
2532:.
2528::
2504:.
2490::
2303:5
2201:.
2179::
2151:.
2147::
2095::
2065:.
2045::
2000:.
1988::
1953:.
1941::
1914:.
1908::
1862:.
1842::
1834::
1789:.
1749:.
1745::
1721:.
1717::
1694:.
1682::
1676:3
1659:.
1647::
1624:.
1620::
1597:.
1583::
1564:.
1560::
1538:.
1516:.
1512::
1506:9
1498:2
1494:2
1492:H
1490:6
1488:C
1486:3
1482:2
1480:H
1478:6
1476:C
1474:3
1470:2
1455::
1226:2
1222:R
1208:1
1204:R
1170:X
1157:2
1153:R
1149:+
1139:2
1121:1
1117:R
1099:-
1087:-
1035:2
837:3
833:4
829:3
722:3
666:2
654:2
644:4
532:2
530:)
528:3
524:3
520:2
479:2
477:R
471:2
452:2
448:2
405:5
403:H
401:5
375:H
371:B
369:2
317:n
311:)
305:n
297:8
293:2
285:2
281:2
276:2
268:2
266:H
264:2
262:B
260:4
258:)
256:3
252:2
250:H
248:6
233:2
229:2
221:2
213:2
184:H
182:n
75:3
20:)
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