468:
768:
614:
666:
173:
629:
647:
430:
553:
507:
266:
390:
538:
568:
365:
295:
155:
496:
2317:
463:
compounds. The dimer could show a certain stability if prepared in an independent way. Bulkier substituents are able to reduce the polymerization rate by steric effect. More steric hindrance could even stop the polymerization or dimerization reactions and renders a germylene thermodynamically stable.
731:
couples are of great significance to the transition metal catalysis. Due to the electronic structure and chemical properties of germylenes, including the empty p-orbital, germylenes are able to activated small molecules and give the corresponding Ge(IV) complexes, which raised researchers' interests
740:. However, subsequent regeneration of Ge(II) compound through reductive elimination is not thermodynamically favored for germylenes. The key of germylene catalysis chemistry is to maintain a balance between oxidative addition and reductive elimination. One example of germylene catalyzed reaction is
533:
process under thermal and photolytical conditions. An identical mechanism through a caged singlet radical pair was proposed for C-Cl bond insertion. However, the interaction between halogen electrons and empty p-orbital of the germylene may result in the formation of a donor-acceptor complex before
20:
278:
The introduction of heteroatom in the ligand backbone enhances the stability of reactive Ge(II) center by electron donation from N lone pair to vacant p-orbitals of germanium center. Typically, the strategy for synthesizing five-membered N-heterocyclic tetrylene involves the reaction between
233:
N, O, P substituents which have lone pairs in that they provide less electronic perturbations. As a result, a stronger steric and electronic stabilization is required to guarantee a monomeric product. Carbon substituted germylenes can be synthesized using various methods: (1)
291:. In the case of n-heterocyclic germylene (NHGe) synthesis, the method involves an initial reduction of N-substituted 1,4-diaza-1,3-butadiene by lithium. The following cyclization of the dianion with the corresponding Ge(II) halides gives the final product.
212:
ligand or of nitrogen (N), oxygen (O) or phosphorus (P) containing ligands, which are able to donate electrons and thus deactivate the vacant p-orbitals. At the same time, stabilization can be accomplished by steric protection of bulky R groups like
1783:"Subvalent Group 4B metal alkyls and amides. Part 8. Germanium and tin carbene analogues MR2[M = Ge or Sn, R = CH(SiMe3)2]: syntheses and structures in the gas phase (electron diffraction); molecular-orbital calculations for MH2 and GeMe2"
1937:
381:
stabilized germylene in a relatively high yield by the reaction between hafnocene dichloride and dipotassium germacyclopentadienediide in THF at -80 °C. The product is stabilized by a remote interaction between a C=C
103:
Ge was found to be: H-Ge-H 93° and C-Ge-C: 98°, which is smaller than 120°, the ideal bond angle for sp hybridized structure and thus proves the 4s4p valence electron configuration nature of germylene. The
698:
N and RCl interact with the vacant p-orbital at germanium center, which could stabilize the singlet germylene and prevent further polymerization. Most of the complexes are stable in room temperature. The
2201:"Chemistry of heavy carbene analogs R2M (M = Si, Ge, Sn). 8. Germylenes: singlets or triplets? [2 + 4]Cheletropic cycloadditions of dimethylgermylene and diiodogermylene to conjugated dienes"
595:
Ge does not have a noticeable activation energy barrier and is only controlled by diffusion. As a result, addition reactions should be rapid enough complete before getting polygermanes as products.
682:
with donors, the germylenes stay in the singlet ground state, where the lone pair is placed in the high-s-character orbital, while the heteroatom-containing donors like R
1331:"Stable Cyclic (Alkyl)(Amino)Carbenes as Rigid or Flexible, Bulky, Electron-Rich Ligands for Transition-Metal Catalysts: A Quaternary Carbon Atom Makes the Difference"
2003:"Chemistry of heavy carbene analogs R2M (M = Si, Ge, Sn). 12. Concerted and nonconcerted insertion reactions of dimethylgermylene into the carbon-halogen bond"
703:
of adducts commonly exhibits shorter wavelengths in comparison to those of the free germylenes due to substituent-influenced n-p transitions at the Ge center.
386:
and vacant p-orbital of Ge center through homoconjugation. This stabilization strategy results in a special structural which possesses unusual reactivity.
1619:"Coinage Metal Complexes of Bis-Alkynyl-Functionalized N-Heterocyclic Carbenes: Reactivity, Photophysical Properties, and Quantum Chemical Investigations"
492:
Ge insertion. The strained C-Ge bonds allow insertion of germylene to 7,7-dialkyl-7-germanorbornadienes in the melt, forming digermabicy-clooctadienes.
1617:
Kiefer, Claude; Bestgen, Sebastian; Gamer, Michael T.; Kühn, Michael; Lebedkin, Sergei; Weigend, Florian; Kappes, Manfred M.; Roesky, Peter W. (2017).
2383:
2076:"Electronic absorption spectra of diorganogermylenes in matrixes: formation of diorganogermylene complexes with heteroatom-containing substrates"
1658:"Multimetallic Complexes Featuring a Bridging N -heterocyclic Phosphido/Phosphenium Ligand: Synthesis, Structure, and Theoretical Investigation"
2470:"Efficient Reduction of Carbon Dioxide to Methanol Equivalents Catalyzed by Two-Coordinate Amido–Germanium(II) and −Tin(II) Hydride Complexes"
1494:"Exploiting Electrostatics To Generate Unsaturation: Oxidative GeE Bond Formation Using a Non π-Donor Stabilized [R(L)Ge:] + Cation"
1445:
Del Rio, Natalia; Baceiredo, Antoine; Saffon-Merceron, Nathalie; Hashizume, Daisuke; Lutters, Dennis; Müller, Thomas; Kato, Tsuyoshi (2016).
1262:
503:
C-H bonds are generally unreactive toward germylene insertion. However, strain release may help to overcome the activation energy barrier.
488:
into C-C bonds has not been reported so far. However, going down the group 14, C-E (E = Si, Ge, Sn, Pb) bonds become more accessible for R
588:
2512:
2279:"The first synthesis of aza-germacyclopentenes: Cycloadditions of 1-aza- and 1,4-diazabutadienes with free singlet dimethyl germylene"
419:
75:
Bonding situation for germylene is distinctively different from that for its light analog carbene. The carbon atom from carbene is sp
158:
Orbitals and electron configuration of triplet carbene and singlet germylene, double donor-acceptor interaction in a germylene dimer
2399:
716:
403:
243:
1860:"Bis(2,4,6-tri-t-butylphenyl)germylen und Bis(2,4,6-tri-t-butylphenyl)germathion: Isomerisierung durch spontane C,H-Insertion"
189:
418:
source. A PNHNHP ligand was used to synthesize the PGeP pincer stabilized germylene by treatment with two equivalents of
1703:
Marchand, Annette; Gerval, Pierre; Duboudin, Françoise; Gaufryau, M.-H.; Joanny, Marguerite; Mazerolles, Pierre (1984).
1572:"Cyclometalated Phosphine-Based Pincer Complexes: Mechanistic Insight in Catalysis, Coordination, and Bond Activation"
209:
1899:"Dimethyl germylene insertion into a strained C-Ge bond and matrix isolation of tetramethyl digermene Me2Ge=GeMe2"
1897:
Bleckmann, Paul; Minkwitz, Rolf; Neumann, Wilhelm P.; Schriewer, Michael; Thibud, Manfred; Watta, Bärbel (1984).
526:
530:
259:
55:, germylenes have exclusively a singlet ground state. Unprotected carbene analogs, including germylenes, has a
204:
originating from the vacant p-orbital. Thermodynamical stabilization of this p-orbital is usually realized by
2154:"Regiospecific Synthesis of Vinylgermyl Compounds from Alkynes or Allenes and Free Singlet Dimethylgermylene"
1781:
Fjeldberg, Torgny; Haaland, Arne; Schilling, Birgitte E. R.; Lappert, Michael F.; Thorne, Andrew J. (1986).
406:
based germylene is of great importance not only for their ability to stabilize transition metal species via
1656:
Pan, Baofei; Evers-McGregor, Deirdra A.; Bezpalko, Mark W.; Foxman, Bruce M.; Thomas, Christine M. (2013).
1243:"N-heterocyclic germylenes and stannylenes: Synthesis, reactivity and catalytic application in a nutshell"
749:
201:
88:
200:
once they form. Free germylenes have to be stabilized kinetically or thermodynamically due to their high
724:
607:
411:
378:
353:
of the germanium center can be obviously enhanced by the substitution of a π-donating and σ-withdrawing
334:
255:
80:
76:
1130:
679:
205:
659:
523:
239:
185:
1705:"Mise en evidence de la formation de R2MMR2 a partir de disila-1,2 et digerma-1,2 cyclohexenes-4"
621:
A variety of 1,2-substituted-vinylgermyl compounds can be synthesized in both high yield and high
2181:
1268:
1242:
720:
485:
92:
2041:
514:
Insertion to carbon-halide bonds is common for germylene. The mechanism for insertion of free Me
1204:
2489:
2450:
2442:
2403:
2364:
2356:
2298:
2259:
2220:
2173:
2134:
2095:
2022:
1980:
1918:
1879:
1837:
1798:
1763:
1724:
1685:
1677:
1638:
1599:
1591:
1552:
1513:
1474:
1466:
1427:
1409:
1368:
1350:
1311:
1258:
1185:
1146:
1099:
1060:
1021:
933:
889:
850:
842:
580:
307:
251:
181:
116:
56:
1618:
1532:
1493:
913:
869:
67:. The synthesis of first stable free dialkyl germylene was reported by Jutzi, et al in 1991.
2481:
2434:
2395:
2348:
2290:
2251:
2212:
2165:
2126:
2087:
2053:
2014:
1972:
1910:
1871:
1829:
1790:
1755:
1716:
1669:
1630:
1583:
1544:
1505:
1458:
1417:
1399:
1358:
1342:
1301:
1290:"One-Pot Synthesis of Heavier Group 14 N-Heterocyclic Carbene Using Organosilicon Reductant"
1250:
1216:
1177:
1138:
1091:
1052:
1041:"Synthesis and solid-state structure of (Me3Si)3CGeCH(SiMe3)2, a monomeric dialkylgermylene"
1013:
967:
925:
881:
834:
733:
622:
109:
1961:"Insertion reactions of dimethylgermylene, Me2Ge, and their mechanisms as studied by CIDNP"
2337:"Main Group Redox Catalysis: Reversible P III /P V Redox Cycling at a Phosphorus Platform"
737:
700:
1329:
Lavallo, Vincent; Canac, Yves; Präsang, Carsten; Donnadieu, Bruno; Bertrand, Guy (2005).
2468:
Hadlington, Terrance J.; Kefalidis, Christos E.; Maron, Laurent; Jones, Cameron (2017).
1134:
1080:"Structure and singlet-triplet separation in simple germylenes GeH2, GeF2, and Ge(CH3)2"
1938:"THE GENERATION AND REACTIONS OF DIMETHYLSILYLENE AND DIMETHYLGERMYLENE IN VAPOR-PHASE"
1422:
1387:
1363:
1330:
785:
761:
654:
Germylenes reacts only with one of the strained double bonds in cumulated systems like
358:
303:
284:
197:
84:
64:
60:
36:
2294:
2255:
1914:
1875:
1759:
1288:
Raut, Ravindra; Amin, Sheikh; Sahoo, Padmini; Kumar, Vikas; Majumdar, Moumita (2018).
1181:
1078:
Barthelat, Jean Claude; Roch, Bruno Saint; Trinquier, Georges; Satge, Jacques (1980).
2506:
2057:
1720:
1272:
1142:
741:
636:
315:
311:
48:
44:
2469:
2185:
2278:
2239:
1898:
1859:
1743:
1165:
1040:
1001:
519:
415:
350:
280:
1704:
1531:
Dong, Zhaowen; Reinhold, Crispin R. W.; Schmidtmann, Marc; Müller, Thomas (2016).
1118:
591:
systems is well studied. As mentioned above, dimerization and polymerization of Me
1254:
302:
The cyclic(alkyl)(amino)carbenes (CAACs) has already been known as both a better
254:
of strained cyclogermanes or Ge(IV) species, (3) substitution of a dihalo Ge(II)
383:
342:
218:
52:
549:
compounds go by a one-step mechanism under thermal or photolytical conditions.
108:
of germylene tends to stay in the high-s-character orbital which is relatively
1404:
1306:
1289:
795:
230:
214:
132:
128:
2493:
2485:
2446:
2422:
2360:
2336:
2302:
2263:
2224:
2177:
2138:
2115:"Germacyclopentanes via cycloadditions of free dimethylgermylene to styrenes"
2099:
2026:
1984:
1922:
1883:
1841:
1802:
1767:
1728:
1681:
1657:
1595:
1571:
1470:
1413:
1354:
1315:
1220:
1189:
1150:
1103:
1064:
1025:
955:
937:
893:
846:
822:
1817:
1446:
712:
426:·dioxane, which finally leads to the formation of the PGeP pincer compound.
407:
321:
The synthetic strategy of CAAGe involves the synthesis of a α-β-unsaturated
148:
105:
28:
2454:
2423:"Diarylstannylene Activation of Hydrogen or Ammonia with Arene Elimination"
2407:
2368:
1833:
1689:
1642:
1634:
1603:
1556:
1548:
1517:
1509:
1478:
1462:
1431:
1372:
1346:
929:
885:
854:
2153:
1782:
598:
There is no reaction between simple alkenes and free germylenes. However,
2400:
10.1002/1521-3773(20020415)41:8<1290::AID-ANIE1290>3.0.CO;2-Y
2200:
2169:
2114:
2075:
2002:
1960:
1818:"ChemInform Abstract: Unsaturated Molecules Containing Main Group Metals"
1794:
1386:
Wang, Liliang; Lim, Yi; Li, Yongxin; Ganguly, Rakesh; Kinjo, Rei (2016).
1079:
790:
757:
564:
Ge insertion product could only remain stable at a very low temperature.
2216:
2130:
2091:
2018:
1976:
1742:
Collins, Scott; Murakami, Shu; Snow, James T.; Masamune, Satoru (1985).
1164:
Collins, Scott; Murakami, Shu; Snow, James T.; Masamune, Satoru (1985).
1095:
1056:
1017:
467:
767:
665:
655:
613:
599:
274:
Synthesis of n-heterocyclic germylene and cyclic(alkyl)(amino)germylene
193:
136:
40:
2438:
2352:
2240:"Additions of free dimethylgermylene to vinyl ketones and α-diketones"
1673:
1587:
1447:"A Stable Heterocyclic Amino(phosphanylidene-σ-phosphorane) Germylene"
971:
870:"Encyclopedia of Inorganic Chemistry. 2nd ed. Edited by R. Bruce King"
838:
628:
172:
2421:
Peng, Yang; Ellis, Bobby D.; Wang, Xinping; Power, Philip P. (2008).
546:
326:
288:
144:
140:
914:"Silylated Group 14 Ylenes: An Emerging Class of Reactive Compounds"
646:
429:
2384:"N-heterocyclic carbene: a new concept in organometallic catalysis"
821:
Mizuhata, Yoshiyuki; Sasamori, Takahiro; Tokitoh, Norihiro (2009).
552:
59:
nature. Free germylenes can be isolated under the stabilization of
2322:
Proceedings of the
Academy of Sciences of the USSR Series Chemical
1744:"Generation and reactivity of bis(2,6-diethylphenyl)germanium(II)"
1205:"Über Aromatenkomplexe von Metallen. IV. Di-cyclopentadienyl-blei"
1166:"Generation and reactivity of bis(2,6-diethylphenyl)germanium(II)"
766:
728:
664:
645:
640:
627:
612:
566:
551:
536:
506:
505:
494:
466:
428:
389:
388:
363:
354:
330:
322:
293:
265:
264:
235:
171:
153:
18:
2001:
Koecher, Juergen.; Lehnig, Manfred.; Neumann, Wilhelm P. (1988).
567:
537:
364:
294:
154:
19:
2152:
Billeb, Gilbert; Brauer, Hartmut; Neumann, Wilhelm P. (1990).
495:
115:
Dimerization of germylenes lead to the formation of germylene
2335:
Dunn, Nicole L.; Ha, Minji; Radosevich, Alexander T. (2012).
455:
dimers which could further polymerize to form polygermanes (R
2074:
Ando, Wataru.; Itoh, Hiroyuki.; Tsumuraya, Takeshi. (1989).
1039:
Jutzi, P.; Becker, A.; Stammler, H. G.; Neumann, B. (1991).
643:
by free germylenes gives the corresponding 5-membered ring.
2316:
Nefedov, O. M.; Kolesnikov, S. P.; Rogozhin, I. S. (1980).
180:
Dimerization of free germylenes does not have a noticeable
2040:
Billeb, G.; Brauer, H.; Maslov, S.; Neumann, W.P. (1989).
373:
Synthesis of a unique homoconjugation stabilized germylene
2042:"Chemie der schweren Carben-Analogen R2M, M = Si, Ge, Sn"
1858:
Lange, Lutz; Meyer, Bernd; du Mont, Wolf-Walther (1987).
377:
In 2016, Muller et al reported the synthesis of a unique
2318:"Molecular complexes of germylene with n-donor ligands"
1119:"Restricted hartree—fock calculations on GeH2 and SnH2"
610:
of 3,4-diphenyl-3,4-R-1,1-dimethyl-1-germacyclopentane.
184:, which means that the dimerization reaction is almost
310:
than n-heterocyclic carbenes (NHCs) due to its higher
131:
between germanium atoms are not necessarily classical
954:
Gaspar, P. P. (1985). Moss, R. A.; Jones, M. (eds.).
447:
Dimerization of carbon substituted germylenes gives R
1787:
Journal of the
Chemical Society, Dalton Transactions
602:
and α-substituted styrenes are able to react with Me
1492:Rit, Arnab; Tirfoin, Rémi; Aldridge, Simon (2016).
393:
Synthesis of a homoconjugation stabilized germylene
606:Ge. The resulting product is a 1:1 mixture of the
556:Reaction for insertion into C-Hal bonds in alkynes
541:Reaction mechanisms for insertion into C-Hal bonds
2199:Schriewer, Michael; Neumann, Wilhelm P. (1983).
1570:van der Boom, Milko E.; Milstein, David (2003).
775:using germylene catalyst and its catalytic cycle
316:lower lowest unoccupied molecular orbital (LUMO)
196:without stabilization could dimerize or further
1388:"Isolation of a Cyclic (Alkyl)(amino)germylene"
534:occurrence of any of the insertion mechanisms.
345:. The resulting product is then reduced with KC
658:(C=C=C). Germylenes prefer to react with more
2238:Michels, Erhard; Neumann, Wilhelm P. (1986).
2113:Koecher, Jurgen; Neumann, Wilhelm P. (1985).
238:of dibromogermanes with reducing agents like
87:for germanium permits the retainment of 4s4p
8:
1249:, vol. 74, Elsevier, pp. 105–152,
471:Dimerization and polymerization of germylene
229:Carbon substituents is different from other
221:from getting close to the germanium center.
31:(II) compounds with the general formula :GeR
2277:Bootz, Konrad; Neumann, Wilhelm P. (1989).
1533:"A Germylene Stabilized by Homoconjugation"
279:N-substituted 1,4-diaza-1,3-butadiene, the
1959:Koecher, Juergen; Lehnig, Manfred (1984).
1241:Dasgupta, Rajarshi; Khan, Shabana (2020),
225:Synthesis of carbon substituted germylenes
1421:
1403:
1362:
1305:
312:highest occupied molecular orbital (HOMO)
83:character, the larger energy gap between
79:. Although germylenes still have some sp
2427:Journal of the American Chemical Society
2341:Journal of the American Chemical Society
2205:Journal of the American Chemical Society
1084:Journal of the American Chemical Society
176:Thermodynamic stabilization of germylene
112:, making germylene exclusively singlet.
1537:Angewandte Chemie International Edition
1498:Angewandte Chemie International Edition
1451:Angewandte Chemie International Edition
1335:Angewandte Chemie International Edition
1203:Fischer, E. O.; Grubert, H. Z. (1956).
918:European Journal of Inorganic Chemistry
874:Angewandte Chemie International Edition
806:
522:bromide was reported to be a two-step,
269:Synthetic methods for stable germylenes
764:to regenerate the germylene compound.
650:Addition to conjugated (hetero-)dienes
420:potassium hexamethyldisilazide (KHMDS)
349:to give CAAGe. Analogous to CAAC, the
2069:
2067:
1996:
1994:
1936:Nefedov, O. M.; Skell, P. S. (1981).
1853:
1851:
1283:
1281:
1236:
1234:
1232:
1230:
756:step is followed by the formation of
625:by addition of germylene to alkynes.
545:The insertion into the C-Hal bond in
414:, but also for its serving as a good
7:
1247:Advances in Organometallic Chemistry
995:
993:
991:
989:
987:
985:
983:
981:
966:(7). New York: J. Wiley: 1199–1200.
949:
947:
907:
905:
903:
816:
814:
812:
810:
2046:Journal of Organometallic Chemistry
1864:Journal of Organometallic Chemistry
1709:Journal of Organometallic Chemistry
337:followed by the treatment with GeCl
43:, whose ground state can be either
868:Sasamori, T.; Tokitoh, N. (2005).
823:"Stable Heavier Carbene Analogues"
443:Oligomerization and polymerization
433:Synthesis of PGeP pincer compounds
398:Synthesis of PGeP pincer compounds
14:
760:derivatives with 3 equivalent of
143:), but can rather be regarded as
16:Class of germanium (II) compounds
210:pentamethylcyclopentadiene (Cp*)
576:Addition to unsaturated systems
258:species with nucleophiles like
1623:Chemistry - A European Journal
23:General structure of germylene
1:
2295:10.1016/s0040-4039(00)70646-0
2256:10.1016/s0040-4039(00)84554-2
1915:10.1016/s0040-4039(01)81206-5
1876:10.1016/s0022-328x(00)99800-0
1760:10.1016/s0040-4039(00)94870-6
1182:10.1016/s0040-4039(00)94870-6
912:Marschner, Christoph (2015).
727:, along with the related M/M
711:Germylenes could also act as
139:as found for carbene dimers (
2058:10.1016/0022-328X(89)85019-3
1721:10.1016/0022-328x(84)80162-x
1255:10.1016/bs.adomc.2020.04.001
1143:10.1016/0009-2614(80)85214-6
1002:"Germylenes and stannylenes"
1000:Neumann, Wilhelm P. (1991).
956:"Reactive Intermediates III"
707:Germylene catalyzed reaction
1117:Olbrich, Gottfried (1980).
960:Journal of Natural Products
2529:
1942:Doklady Akademii Nauk SSSR
240:lithium naphthalene (LiNp)
27:Germylenes are a class of
2513:Organogermanium compounds
1405:10.3390/molecules21080990
1307:10.3390/inorganics6030069
732:in germylenes' acting as
518:Ge into the C-Br bond of
2486:10.1021/acscatal.6b03306
2382:Herrmann, W. A. (2002).
1221:10.1002/zaac.19562860507
1123:Chemical Physics Letters
499:Insertion into C-Ge bond
192:, so the free germylene
639:of conjugated (hetero-)
571:Insertion into C-O bond
510:Insertion into C-H bond
1834:10.1002/chin.198718388
1635:10.1002/chem.201604292
1549:10.1002/anie.201609576
1510:10.1002/anie.201508940
1463:10.1002/anie.201511956
1347:10.1002/anie.200501841
930:10.1002/ejic.201500495
886:10.1002/anie.200585394
776:
748:, where a preliminary
674:Complexation by donors
670:
651:
633:
618:
572:
557:
542:
511:
500:
472:
434:
394:
369:
357:along with σ-donating
299:
270:
260:organometallic ligands
244:potassium graphite (KC
177:
159:
145:donor–acceptor adducts
89:electron configuration
71:Structures and bonding
24:
770:
725:reductive elimination
668:
649:
631:
616:
570:
555:
540:
509:
498:
476:Insertion into σ bond
470:
432:
412:homogeneous catalysis
392:
367:
359:trimethylsilyl groups
297:
268:
175:
157:
127:). It was found that
22:
2170:10.1055/s-1990-21006
1795:10.1039/dt9860001551
617:Addition to styrenes
608:syn and anti-isomers
215:mesityl groups (Mes)
149:trans-bent structure
91:to some degree. The
2433:(37): 12268–12269.
2347:(28): 11330–11333.
2283:Tetrahedron Letters
2244:Tetrahedron Letters
2217:10.1021/ja00342a043
2131:10.1021/om00121a038
2092:10.1021/om00114a004
2019:10.1021/om00095a029
1977:10.1021/om00084a022
1903:Tetrahedron Letters
1748:Tetrahedron Letters
1662:Inorganic Chemistry
1543:(51): 15899–15904.
1170:Tetrahedron Letters
1135:1980CPL....73..110O
1096:10.1021/ja00532a017
1057:10.1021/om00052a002
1018:10.1021/cr00003a002
771:Hydroboration of CO
669:Addition to allenes
632:Addition to alkynes
35:. They are heavier
1816:VEITH, M. (1987).
777:
721:Oxidative addition
671:
660:electron-deficient
652:
634:
619:
573:
558:
543:
512:
501:
473:
435:
395:
370:
368:Synthesis of CAAGe
300:
271:
262:(e.g. RLi/RMgBr).
178:
160:
39:. However, unlike
25:
2439:10.1021/ja805358u
2388:Angew Chem Int Ed
2353:10.1021/ja302963p
2289:(48): 6669–6672.
2250:(22): 2455–2458.
2086:(12): 2759–2766.
1909:(23): 2467–2470.
1754:(10): 1281–1284.
1674:10.1021/ic4012873
1668:(16): 9583–9589.
1588:10.1021/cr960118r
1457:(15): 4753–4758.
1341:(35): 5705–5709.
1264:978-0-12-820692-8
1176:(10): 1281–1284.
1090:(12): 4080–4085.
972:10.1021/np030742g
924:(23): 3805–3820.
880:(36): 1698–1740.
839:10.1021/cr900093s
734:spectator ligands
717:transition metals
637:1,4-Cycloaddition
581:Addition reaction
408:chelation effects
298:Synthesis of NHGe
190:diffusion limited
65:electron donation
51:depending on the
2520:
2498:
2497:
2480:(3): 1853–1859.
2465:
2459:
2458:
2418:
2412:
2411:
2394:(8): 1290–1309.
2379:
2373:
2372:
2332:
2326:
2325:
2313:
2307:
2306:
2274:
2268:
2267:
2235:
2229:
2228:
2196:
2190:
2189:
2149:
2143:
2142:
2110:
2104:
2103:
2071:
2062:
2061:
2037:
2031:
2030:
2013:(5): 1201–1207.
1998:
1989:
1988:
1956:
1950:
1949:
1933:
1927:
1926:
1894:
1888:
1887:
1855:
1846:
1845:
1813:
1807:
1806:
1778:
1772:
1771:
1739:
1733:
1732:
1700:
1694:
1693:
1653:
1647:
1646:
1629:(7): 1591–1603.
1614:
1608:
1607:
1582:(5): 1759–1792.
1576:Chemical Reviews
1567:
1561:
1560:
1528:
1522:
1521:
1489:
1483:
1482:
1442:
1436:
1435:
1425:
1407:
1383:
1377:
1376:
1366:
1326:
1320:
1319:
1309:
1285:
1276:
1275:
1238:
1225:
1224:
1215:(5–6): 237–242.
1200:
1194:
1193:
1161:
1155:
1154:
1114:
1108:
1107:
1075:
1069:
1068:
1051:(6): 1647–1648.
1036:
1030:
1029:
1006:Chemical Reviews
997:
976:
975:
951:
942:
941:
909:
898:
897:
865:
859:
858:
833:(8): 3479–3511.
827:Chemical Reviews
818:
750:hydrogermylation
738:catalytic cycles
701:absorption bands
623:regioselectivity
351:electrophilicity
85:s and p-orbitals
61:steric hindrance
2528:
2527:
2523:
2522:
2521:
2519:
2518:
2517:
2503:
2502:
2501:
2467:
2466:
2462:
2420:
2419:
2415:
2381:
2380:
2376:
2334:
2333:
2329:
2315:
2314:
2310:
2276:
2275:
2271:
2237:
2236:
2232:
2198:
2197:
2193:
2151:
2150:
2146:
2119:Organometallics
2112:
2111:
2107:
2080:Organometallics
2073:
2072:
2065:
2039:
2038:
2034:
2007:Organometallics
2000:
1999:
1992:
1965:Organometallics
1958:
1957:
1953:
1935:
1934:
1930:
1896:
1895:
1891:
1857:
1856:
1849:
1815:
1814:
1810:
1780:
1779:
1775:
1741:
1740:
1736:
1702:
1701:
1697:
1655:
1654:
1650:
1616:
1615:
1611:
1569:
1568:
1564:
1530:
1529:
1525:
1491:
1490:
1486:
1444:
1443:
1439:
1385:
1384:
1380:
1328:
1327:
1323:
1287:
1286:
1279:
1265:
1240:
1239:
1228:
1202:
1201:
1197:
1163:
1162:
1158:
1116:
1115:
1111:
1077:
1076:
1072:
1045:Organometallics
1038:
1037:
1033:
999:
998:
979:
953:
952:
945:
911:
910:
901:
867:
866:
862:
820:
819:
808:
804:
786:Carbene analogs
782:
774:
755:
747:
709:
697:
693:
689:
685:
676:
605:
594:
586:
578:
563:
517:
491:
483:
478:
462:
458:
454:
450:
445:
440:
425:
400:
379:homoconjugation
375:
348:
340:
285:reducing agents
276:
247:
227:
170:
165:
126:
122:
102:
98:
73:
37:carbene analogs
34:
17:
12:
11:
5:
2526:
2524:
2516:
2515:
2505:
2504:
2500:
2499:
2460:
2413:
2374:
2327:
2308:
2269:
2230:
2211:(4): 897–901.
2191:
2164:(3): 113–114.
2144:
2125:(2): 400–402.
2105:
2063:
2032:
1990:
1971:(6): 937–939.
1951:
1928:
1889:
1870:(2): C17–C20.
1847:
1808:
1773:
1734:
1695:
1648:
1609:
1562:
1523:
1504:(1): 378–382.
1484:
1437:
1378:
1321:
1277:
1263:
1226:
1195:
1156:
1129:(1): 110–113.
1109:
1070:
1031:
1012:(3): 311–334.
977:
943:
899:
860:
805:
803:
800:
799:
798:
793:
788:
781:
778:
772:
762:catecholborane
753:
745:
708:
705:
695:
691:
687:
683:
675:
672:
603:
592:
584:
577:
574:
561:
560:For C-O, the R
515:
489:
481:
477:
474:
460:
456:
452:
448:
444:
441:
439:
436:
423:
399:
396:
374:
371:
346:
338:
275:
272:
245:
226:
223:
182:energy barrier
169:
166:
164:
161:
129:multiple bonds
124:
120:
100:
96:
72:
69:
32:
15:
13:
10:
9:
6:
4:
3:
2:
2525:
2514:
2511:
2510:
2508:
2495:
2491:
2487:
2483:
2479:
2475:
2474:ACS Catalysis
2471:
2464:
2461:
2456:
2452:
2448:
2444:
2440:
2436:
2432:
2428:
2424:
2417:
2414:
2409:
2405:
2401:
2397:
2393:
2389:
2385:
2378:
2375:
2370:
2366:
2362:
2358:
2354:
2350:
2346:
2342:
2338:
2331:
2328:
2323:
2319:
2312:
2309:
2304:
2300:
2296:
2292:
2288:
2284:
2280:
2273:
2270:
2265:
2261:
2257:
2253:
2249:
2245:
2241:
2234:
2231:
2226:
2222:
2218:
2214:
2210:
2206:
2202:
2195:
2192:
2187:
2183:
2179:
2175:
2171:
2167:
2163:
2159:
2155:
2148:
2145:
2140:
2136:
2132:
2128:
2124:
2120:
2116:
2109:
2106:
2101:
2097:
2093:
2089:
2085:
2081:
2077:
2070:
2068:
2064:
2059:
2055:
2051:
2048:(in German).
2047:
2043:
2036:
2033:
2028:
2024:
2020:
2016:
2012:
2008:
2004:
1997:
1995:
1991:
1986:
1982:
1978:
1974:
1970:
1966:
1962:
1955:
1952:
1948:(2): 377–379.
1947:
1943:
1939:
1932:
1929:
1924:
1920:
1916:
1912:
1908:
1904:
1900:
1893:
1890:
1885:
1881:
1877:
1873:
1869:
1865:
1861:
1854:
1852:
1848:
1843:
1839:
1835:
1831:
1827:
1823:
1819:
1812:
1809:
1804:
1800:
1796:
1792:
1788:
1784:
1777:
1774:
1769:
1765:
1761:
1757:
1753:
1749:
1745:
1738:
1735:
1730:
1726:
1722:
1718:
1715:(1): 93–106.
1714:
1710:
1706:
1699:
1696:
1691:
1687:
1683:
1679:
1675:
1671:
1667:
1663:
1659:
1652:
1649:
1644:
1640:
1636:
1632:
1628:
1624:
1620:
1613:
1610:
1605:
1601:
1597:
1593:
1589:
1585:
1581:
1577:
1573:
1566:
1563:
1558:
1554:
1550:
1546:
1542:
1538:
1534:
1527:
1524:
1519:
1515:
1511:
1507:
1503:
1499:
1495:
1488:
1485:
1480:
1476:
1472:
1468:
1464:
1460:
1456:
1452:
1448:
1441:
1438:
1433:
1429:
1424:
1419:
1415:
1411:
1406:
1401:
1397:
1393:
1389:
1382:
1379:
1374:
1370:
1365:
1360:
1356:
1352:
1348:
1344:
1340:
1336:
1332:
1325:
1322:
1317:
1313:
1308:
1303:
1299:
1295:
1291:
1284:
1282:
1278:
1274:
1270:
1266:
1260:
1256:
1252:
1248:
1244:
1237:
1235:
1233:
1231:
1227:
1222:
1218:
1214:
1210:
1206:
1199:
1196:
1191:
1187:
1183:
1179:
1175:
1171:
1167:
1160:
1157:
1152:
1148:
1144:
1140:
1136:
1132:
1128:
1124:
1120:
1113:
1110:
1105:
1101:
1097:
1093:
1089:
1085:
1081:
1074:
1071:
1066:
1062:
1058:
1054:
1050:
1046:
1042:
1035:
1032:
1027:
1023:
1019:
1015:
1011:
1007:
1003:
996:
994:
992:
990:
988:
986:
984:
982:
978:
973:
969:
965:
961:
957:
950:
948:
944:
939:
935:
931:
927:
923:
919:
915:
908:
906:
904:
900:
895:
891:
887:
883:
879:
875:
871:
864:
861:
856:
852:
848:
844:
840:
836:
832:
828:
824:
817:
815:
813:
811:
807:
801:
797:
794:
792:
789:
787:
784:
783:
779:
769:
765:
763:
759:
751:
743:
742:hydroboration
739:
735:
730:
726:
722:
718:
714:
706:
704:
702:
681:
673:
667:
663:
661:
657:
648:
644:
642:
638:
630:
626:
624:
615:
611:
609:
601:
596:
590:
582:
575:
569:
565:
554:
550:
548:
539:
535:
532:
531:recombination
528:
525:
521:
508:
504:
497:
493:
487:
475:
469:
465:
442:
437:
431:
427:
421:
417:
413:
409:
405:
397:
391:
387:
385:
380:
372:
366:
362:
360:
356:
352:
344:
336:
332:
328:
324:
319:
317:
313:
309:
305:
296:
292:
290:
287:and group 14
286:
282:
273:
267:
263:
261:
257:
253:
249:
241:
237:
232:
224:
222:
220:
216:
211:
207:
203:
199:
195:
191:
187:
183:
174:
168:Stabilization
167:
162:
156:
152:
150:
146:
142:
138:
134:
130:
118:
113:
111:
107:
94:
90:
86:
82:
81:hybridization
78:
70:
68:
66:
62:
58:
54:
50:
46:
42:
38:
30:
21:
2477:
2473:
2463:
2430:
2426:
2416:
2391:
2387:
2377:
2344:
2340:
2330:
2321:
2311:
2286:
2282:
2272:
2247:
2243:
2233:
2208:
2204:
2194:
2161:
2157:
2147:
2122:
2118:
2108:
2083:
2079:
2052:(1): 11–19.
2049:
2045:
2035:
2010:
2006:
1968:
1964:
1954:
1945:
1941:
1931:
1906:
1902:
1892:
1867:
1863:
1825:
1821:
1811:
1786:
1776:
1751:
1747:
1737:
1712:
1708:
1698:
1665:
1661:
1651:
1626:
1622:
1612:
1579:
1575:
1565:
1540:
1536:
1526:
1501:
1497:
1487:
1454:
1450:
1440:
1395:
1391:
1381:
1338:
1334:
1324:
1297:
1293:
1246:
1212:
1208:
1198:
1173:
1169:
1159:
1126:
1122:
1112:
1087:
1083:
1073:
1048:
1044:
1034:
1009:
1005:
963:
959:
921:
917:
877:
873:
863:
830:
826:
710:
680:complexation
677:
653:
635:
620:
597:
579:
559:
544:
513:
502:
479:
446:
416:luminescence
401:
376:
335:condensation
320:
301:
281:alkali metal
277:
250:, etc., (2)
228:
219:nucleophiles
206:coordination
179:
114:
74:
57:dimerization
53:substituents
26:
1789:(8): 1551.
1209:Naturforsch
736:in certain
589:unsaturated
527:abstraction
384:double bond
355:amino group
306:and better
217:to prevent
186:spontaneous
2324:: 170–173.
1822:ChemInform
1398:(8): 990.
1294:Inorganics
802:References
796:Stannylene
438:Reactivity
252:photolysis
231:heteroatom
202:reactivity
198:polymerize
93:bond angle
77:hybridized
2494:2155-5435
2447:0002-7863
2361:0002-7863
2303:0040-4039
2264:0040-4039
2225:0002-7863
2178:0936-5214
2139:0276-7333
2100:0276-7333
2027:0276-7333
1985:0276-7333
1923:0040-4039
1884:0022-328X
1842:0931-7597
1828:(18): 1.
1803:0300-9246
1768:0040-4039
1729:0022-328X
1682:0020-1669
1596:0009-2665
1471:1433-7851
1414:1420-3049
1392:Molecules
1355:1433-7851
1316:2304-6740
1300:(3): 69.
1273:226476659
1190:0040-4039
1151:0009-2614
1104:0002-7863
1065:0276-7333
1026:0009-2665
938:1434-1948
894:1433-7851
847:0009-2665
713:catalysts
686:O, ROH, R
662:allenes.
486:insertion
256:precursor
236:reduction
163:Synthesis
106:lone pair
99:Ge and Me
29:germanium
2507:Category
2455:18714994
2408:19750753
2369:22746974
2186:98481510
1690:23923983
1643:27780290
1604:12744693
1557:27860046
1518:26545498
1479:26954722
1432:27483223
1373:16059961
855:19630390
791:Silylene
780:See also
758:methanol
600:styrenes
422:and GeCl
308:acceptor
194:monomers
41:carbenes
2158:Synlett
1423:6273211
1364:2427276
1131:Bibcode
678:During
656:allenes
524:radical
343:dioxane
329:and an
325:from a
289:halides
141:alkenes
137:π bonds
49:triplet
45:singlet
2492:
2453:
2445:
2406:
2367:
2359:
2301:
2262:
2223:
2184:
2176:
2137:
2098:
2025:
1983:
1921:
1882:
1840:
1801:
1766:
1727:
1688:
1680:
1641:
1602:
1594:
1555:
1516:
1477:
1469:
1430:
1420:
1412:
1371:
1361:
1353:
1314:
1271:
1261:
1188:
1149:
1102:
1063:
1024:
936:
892:
853:
845:
641:dienes
587:Ge to
547:alkyne
520:benzyl
451:Ge=GeR
404:pincer
327:ketone
283:based
123:Ge=GeR
117:dimers
2182:S2CID
1269:S2CID
752:of CO
744:of CO
729:redox
583:of Me
331:amine
323:imine
304:donor
208:of a
147:of a
110:inert
95:for H
2490:ISSN
2451:PMID
2443:ISSN
2404:PMID
2365:PMID
2357:ISSN
2299:ISSN
2260:ISSN
2221:ISSN
2174:ISSN
2162:1990
2135:ISSN
2096:ISSN
2023:ISSN
1981:ISSN
1919:ISSN
1880:ISSN
1838:ISSN
1799:ISSN
1764:ISSN
1725:ISSN
1686:PMID
1678:ISSN
1639:PMID
1600:PMID
1592:ISSN
1553:PMID
1514:PMID
1475:PMID
1467:ISSN
1428:PMID
1410:ISSN
1369:PMID
1351:ISSN
1312:ISSN
1259:ISBN
1186:ISSN
1147:ISSN
1100:ISSN
1061:ISSN
1022:ISSN
934:ISSN
922:2015
890:ISSN
851:PMID
843:ISSN
723:and
719:do.
694:P, R
690:S, R
402:The
333:via
314:and
188:and
135:and
2482:doi
2435:doi
2431:130
2396:doi
2349:doi
2345:134
2291:doi
2252:doi
2213:doi
2209:105
2166:doi
2127:doi
2088:doi
2054:doi
2050:373
2015:doi
1973:doi
1946:259
1911:doi
1872:doi
1868:329
1830:doi
1791:doi
1756:doi
1717:doi
1713:267
1670:doi
1631:doi
1584:doi
1580:103
1545:doi
1506:doi
1459:doi
1418:PMC
1400:doi
1359:PMC
1343:doi
1302:doi
1251:doi
1217:doi
1178:doi
1139:doi
1092:doi
1088:102
1053:doi
1014:doi
968:doi
926:doi
882:doi
835:doi
831:109
715:as
484:Ge
459:Ge)
410:in
318:.
242:or
63:or
47:or
2509::
2488:.
2476:.
2472:.
2449:.
2441:.
2429:.
2425:.
2402:.
2392:41
2390:.
2386:.
2363:.
2355:.
2343:.
2339:.
2320:.
2297:.
2287:30
2285:.
2281:.
2258:.
2248:27
2246:.
2242:.
2219:.
2207:.
2203:.
2180:.
2172:.
2160:.
2156:.
2133:.
2121:.
2117:.
2094:.
2082:.
2078:.
2066:^
2044:.
2021:.
2009:.
2005:.
1993:^
1979:.
1967:.
1963:.
1944:.
1940:.
1917:.
1907:25
1905:.
1901:.
1878:.
1866:.
1862:.
1850:^
1836:.
1826:18
1824:.
1820:.
1797:.
1785:.
1762:.
1752:26
1750:.
1746:.
1723:.
1711:.
1707:.
1684:.
1676:.
1666:52
1664:.
1660:.
1637:.
1627:23
1625:.
1621:.
1598:.
1590:.
1578:.
1574:.
1551:.
1541:55
1539:.
1535:.
1512:.
1502:55
1500:.
1496:.
1473:.
1465:.
1455:55
1453:.
1449:.
1426:.
1416:.
1408:.
1396:21
1394:.
1390:.
1367:.
1357:.
1349:.
1339:44
1337:.
1333:.
1310:.
1296:.
1292:.
1280:^
1267:,
1257:,
1245:,
1229:^
1213:91
1211:.
1207:.
1184:.
1174:26
1172:.
1168:.
1145:.
1137:.
1127:73
1125:.
1121:.
1098:.
1086:.
1082:.
1059:.
1049:10
1047:.
1043:.
1020:.
1010:91
1008:.
1004:.
980:^
964:67
962:.
958:.
946:^
932:.
920:.
916:.
902:^
888:.
878:45
876:.
872:.
849:.
841:.
829:.
825:.
809:^
361:.
151:.
119:(R
2496:.
2484::
2478:7
2457:.
2437::
2410:.
2398::
2371:.
2351::
2305:.
2293::
2266:.
2254::
2227:.
2215::
2188:.
2168::
2141:.
2129::
2123:4
2102:.
2090::
2084:8
2060:.
2056::
2029:.
2017::
2011:7
1987:.
1975::
1969:3
1925:.
1913::
1886:.
1874::
1844:.
1832::
1805:.
1793::
1770:.
1758::
1731:.
1719::
1692:.
1672::
1645:.
1633::
1606:.
1586::
1559:.
1547::
1520:.
1508::
1481:.
1461::
1434:.
1402::
1375:.
1345::
1318:.
1304::
1298:6
1253::
1223:.
1219::
1192:.
1180::
1153:.
1141::
1133::
1106:.
1094::
1067:.
1055::
1028:.
1016::
974:.
970::
940:.
928::
896:.
884::
857:.
837::
773:2
754:2
746:2
696:3
692:3
688:2
684:2
604:2
593:2
585:2
562:2
529:-
516:2
490:2
482:2
480:R
461:n
457:2
453:2
449:2
424:2
347:8
341:·
339:2
248:)
246:8
133:σ
125:2
121:2
101:2
97:2
33:2
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
