649:
24:
399:
441:
711:
553:
671:
698:
is observed between aldehydes or ketones and allyl electrophiles under catalytic conditions. The proposed mechanism involves titanium(III)-mediated generation of an allyl radical species which intercepts a titanium(III)-coordinated carbonyl. Another application involves the single electron reduction
629:
and is not known to occur naturally. However, it can be prepared either from vindoline and catharanthine or from leurosine, in both cases by synthesis of anhydrovinblastine, which "can be considered as the key intermediate for the synthesis of vinorelbine." The leurosine pathway uses the
1161:
Barrero, Alejandro F.; Oltra, J. Enrique; Cuerva, Juan M.; Rosales, Antonio (2002). "Effects of solvents and water in Ti(III)-mediated radical cyclizations of epoxygermacrolides. Straightforward synthesis and absolute stereochemistry of (+)-3α-hydroxyreynosin and related eudesmanolides".
1442:
Clive, D. L. J.; Magnuson, Steven R.; Manning, Hartford W.; Mayhew, Darrin L. (1996). "Cyclopentannulation by an iterative process of sequential
Claisen rearrangement and enyne radical closure: Routes to triquinane and propellane systems and use in the synthesis of (±)-ceratopicanol".
1906:
DiĂ©guez, Horacio R.; LĂłpez, Armando; Domingo, Victoriano; Arteaga, JesĂșs F.; Dobado, JosĂ© A.; Herrador, M. Mar; Moral, JosĂ© F. QuĂlez del; Barrero, Alejandro F. (2010). "Weakening C—O bonds: Ti(III), a new reagent for alcohol deoxygenation and carbonyl coupling olefination".
1806:
Barrero, Alejandro F.; Rosales, Antonio; Cuerva, Juan M.; GansÀuer, Andreas; Oltra, J. Enrique (2003). "Titanocene-catalysed, selective reduction of ketones in aqueous media. A safe, mild, inexpensive procedure for the synthesis of secondary alcohols via radical chemistry".
947:
Rosales, Antonio; RodrĂguez-Garcia, Ignacio; Muñoz-BascĂłn, Juan; Roldan-Molina, Esther; Padial, Natalia M.; Morales, Laura P.; GarcĂa-Ocaña, Marta; Oltra, J. Enrique (2015). "The Nugent
Reagent: A Formidable Tool in Contemporary Radical and Organometallic Chemistry".
2055:
GansĂ€uer, Andreas; Barchuk, Andriy; Keller, Florian; Schmitt, Martin; Grimme, Stefan; Gerenkamp, Mareike; MĂŒck-Lichtenfeld, Christian; Daasbjerg, Kim; Svith, Heidi (2007). "Mechanism of titanocene-mediated epoxide opening through homolytic substitution".
391:
1472:
GansÀuer, Andreas; Pierobon, Marianna; Bluhm, Harald (1998). "Catalytic, highly regio- and chemoselective generation of radicals from epoxides: Titanocene dichloride as an electron transfer catalyst in transition metal catalyzed radical reactions".
1865:
Paradas, Miguel; Campaña, Araceli G.; EstĂ©vez, Rosa E.; Cienfuegos, Luis Ălvarez de; JimĂ©nez, Tania; Robles, Rafael; Cuerva, Juan M.; Oltra, J. Enrique (2009). "Unexpected Ti/Mn-promoted pinacol coupling of ketones".
579:
dig radical cyclization to forge the core of ceratopicanol. Addition of a hydrochloride salt to the reaction facilitates release of the oxygen-bound titanium(IV) intermediate, allowing the reagent to be recycled.
3506:
515:(such as an alkene, alkyne, carbonyl, etc.) is present in the epoxide. Synthesis of natural products with multiple ring systems have taken advantage of this pathway. Intermolecular trapping of
1350:
GansÀuer, Andreas; Pierobon, Marianna; Bluhm, Harald (2002). "Stereoselective synthesis of tri- and tetrasubstituted olefins by tandem cyclization addition reactions featuring vinyl radicals".
1944:
Rosales, Antonio; Oller-López, Juan L.; Justicia, José; GansÀuer, Andreas; Oltra, J. Enrique; Cuerva, Juan M. (2004). "Unprecedented
Barbier-type reactions catalysed by titanocene(III)".
3494:
2971:
95:
1132:
RajanBabu, T. V.; Nugent, William A. (1994). "Selective generation of free radicals from epoxides using a transition-metal radical. A powerful new tool for organic synthesis".
972:
Rosales, Antonio; RodrĂguez-Garcia, Ignacio; Muñoz-BascĂłn, Juan; Roldan-Molina, Esther; Padial, Natalia M.; Morales, Laura P.; GarcĂa-Ocaña, Marta; Oltra, J. Enrique (2015).
849:
Handa, Yuichi; Inanaga, Junji (1987). "A highly stereoselective pinacolization of aromatic and α, ÎČ-unsaturated aldehydes mediated by titanium(III)-magnesium(II) complex".
1725:
Ngo, Quoc Anh; Roussi, Fanny; Cormier, Anthony; Thoret, Sylviane; Knossow, Marcel; Guénard, Daniel; Guéritte, Françoise (2009). "Synthesis and biological evaluation of
915:
Jungst, Rudolph; Sekutowski, Dennis; Davis, Jimmy; Luly, Matthew; Stucky, Galen (1977). "Structural and magnetic properties of di-Ό-chloro-bis and di-Ό-bromo-bis".
747:
and an oxygen bound titanium(IV) species. This process is driven by the strength of the titanium-oxygen bond, as well as strain release in the case of epoxides.
3185:
1232:
Rickborn, Bruce; Lamke, Wallace E. (1967). "Reduction of epoxides. II. The lithium aluminum hydride and mixed hydride reduction of 3-methylcyclohexene oxide".
3470:
2110:
159:
881:
Nugent, William A.; RajanBabu, T. V. (1988). "Transition-metal-centered radicals in organic synthesis. Titanium(III)-induced cyclization of epoxy olefins".
3605:
3217:
2964:
1836:
GansÀuer, Andreas (1997). "Pinacol coupling of aromatic aldehydes catalysed by a titanocene complex: A transition metal catalysed radical reaction".
2058:
1909:
1397:
1323:
1134:
1105:
883:
481:
product. This transformation provides the complementary regioisomer to that of an epoxide opening using a metal hydride; in particular, the use of
459:
intermediate and is tolerant of alcohols and some basic nitrogen functional groups, however it is sensitive to oxidizing functional groups such as
1475:
1352:
743:
and thus binds epoxides and carbonyl compounds. The complex transfers a single electron to the coordinated substrate generating an alkyl centered
463:. As can be seen in the above illustration, subsequent reaction proceeds along a pathway determined by added reagents and reaction conditions:
3322:
3200:
3135:
648:
1488:
3935:
3868:
978:
950:
1769:
Hardouin, Christophe; Doris, Eric; Rousseau, Bernard; Mioskowski, Charles (2002). "Concise synthesis of anhydrovinblastine from leurosine".
2957:
1677:
1071:
1981:
Streuff, Jan (2011). "A titanium(III)-catalyzed redox
Umpolung reaction for the reductive cross-coupling of enones with acrylonitriles".
3930:
1983:
630:
NugentâRajanBabu reagent in a highly chemoselective de-oxygenation of leurosine. Anhydrovinblastine is then reacted sequentially with
3065:
3340:
1655:
1562:
1529:
1199:
Rickborn, Bruce; Quartucci, Joe (1964). "Stereochemistry and mechanism of lithium aluminum hydride and mixed hydride reduction of 4-
1103:
RajanBabu, T. V.; Nugent, William A.; Beattie, Margaret S. (1990). "Free radical-mediated reduction and deoxygenation of epoxides".
1087:
1035:
833:
134:
1365:
2018:
CangönĂŒl, Asli; Behlendorf, Maike; GansĂ€uer, Andreas; Gastel, Maurice van (2013). "Radical-based epoxide opening by titanocenes".
3527:
3357:
2103:
87:
3311:
2403:
402:
The calculated spin density of the ground state singlet biradical (broken symmetry density functional theory, TPSSh/def2-TZVP).
1731:
1272:
Morcillo, Sara P.; Miguel, Delia; Campaña, Araceli G.; Cienfuegos, Luis Ălvarez de; Justicia, JosĂ©; Cuerva, Juan M. (2014).
2020:
917:
1321:
RajanBabu, T. V.; Nugent, William A. (1989). "Intermolecular addition of epoxides to activated olefins: a new reaction".
250:
2826:
1868:
1445:
1234:
1205:
1164:
3094:
2854:
2527:
2096:
282:
703:
type adducts. Benzylic and allylic alcohols can be de-oxygenated under mild conditions using super-stoichiometric Cp
2840:
626:
3940:
3546:
3246:
3012:
2812:
1282:
969:
This review article was corrected to refer to the "NugentâRajanBabu
Reagent" rather than the "Nugent Reagent" by:
687:
482:
448:
23:
3651:
3124:
3052:
2728:
699:
of enones to generate allylic radicals which can undergo intermolecular trapping with acrylonitriles to afford
642:
497:
426:
2949:
308:
between the forms and . It is these forms that are responsible for much of the chemical properties of this
3142:
2927:
2884:
2796:
2672:
2251:
1946:
1838:
508:
270:
3459:
3413:
2772:
2367:
2359:
2339:
2230:
2222:
422:
407:
313:
3447:
3189:
3153:
3112:
3023:
2919:
2575:
2487:
2317:
2268:
2214:
2192:
2133:
347:
3425:
414:
1068:
Metal
Catalyzed Reductive C—C Bond Formation: A Departure from Preformed Organometallic Reagents
974:"The NugentâRajanBabu Reagent: A Formidable Tool in Contemporary Radical and Organometallic Chemistry"
3925:
3590:
3435:
3284:
2636:
2447:
2387:
2379:
2347:
2238:
2170:
2149:
1647:
1019:
778:
664:
638:
384:
305:
312:, which is also the reason that the substance is sometimes written as or , where Cp represents the
2868:
2780:
2712:
2567:
2559:
2330:
2256:
2175:
2157:
1809:
1591:
851:
817:
769:
744:
585:
568:
560:
478:
52:
2892:
2551:
2209:
2165:
2119:
1063:
794:
764:
631:
512:
468:
343:
2931:
1521:
1511:
1273:
602:
3031:
2981:
2503:
2467:
2309:
2075:
2037:
2000:
1963:
1926:
1885:
1788:
1748:
1704:
1651:
1639:
1620:
1558:
1525:
1424:
1369:
1181:
1083:
1031:
829:
372:
293:
274:
1546:
1503:
1059:
1058:
GansÀuer, Andreas; Justicia, José; Fan, Chun-An; Worgull, Dennis; Piestert, Frederik (2007).
2760:
2744:
2700:
2664:
2648:
2427:
2415:
2325:
2246:
2141:
2067:
2029:
1992:
1955:
1918:
1877:
1847:
1818:
1780:
1740:
1694:
1686:
1610:
1600:
1484:
1454:
1414:
1406:
1361:
1332:
1301:
1291:
1243:
1214:
1173:
1143:
1114:
1075:
1023:
987:
959:
926:
892:
860:
821:
786:
700:
695:
691:
675:
531:
486:
418:
398:
187:
3164:
2996:
2923:
2628:
2535:
2395:
1771:
1517:
530:
Another pathway intercepts the radical intermediate with nickel catalysis and facilitates
472:
376:
328:
301:
62:
782:
1699:
1672:
1615:
1586:
1419:
1388:
598:
572:
542:
534:
440:
286:
244:
1822:
1508:
L. (Periwinkle): Production of
Vindoline and Catharanthine in Multiple Shoot Cultures"
864:
714:
Catalytic modification: addition of a mildly acidic HCl salt promotes cleavage of the
120:
3919:
2900:
2876:
740:
660:
618:
590:
564:
520:
798:
500:(favoured for 3° species) or dehydration via ÎČ-alkoxy elimination; in both cases an
3836:
3828:
3820:
3809:
3792:
3784:
3776:
3768:
3752:
3582:
2935:
2435:
1673:"Safety and efficacy of vinorelbine in the treatment of non-small cell lung cancer"
606:
545:
456:
324:
552:
496:
TiCl traps the radical as an alkyl-titanium(IV) species which can either undergo
3486:
3349:
3332:
3261:
3230:
3057:
2688:
1060:"Reductive C—C bond formation after epoxide opening via electron transfer"
622:
614:
610:
460:
362:. For use in organic synthesis, the reagent is often prepared and used directly
320:
1489:
10.1002/(sici)1521-3773(19980202)37:1/2<101::aid-anie101>3.0.co;2-w
1027:
825:
390:
3656:
3551:
3209:
3177:
3104:
1605:
707:
TiCl, however the reported scope for aliphatic alcohols is currently limited.
221:
413:
The compound is also known as the NugentâRajanBabu reagent, after scientists
281:. It is an air sensitive green solid. The complex finds specialized use in
3702:
3634:
3617:
3519:
3397:
3238:
1554:
710:
594:
359:
355:
2079:
2041:
2004:
1996:
1967:
1930:
1889:
1792:
1752:
1708:
1644:
The evolution of drug discovery: From traditional medicines to modern drugs
1624:
1428:
1373:
1185:
992:
973:
963:
1366:
10.1002/1521-3773(20020902)41:17<3206::AID-ANIE3206>3.0.CO;2-2
735:
The dimeric titanium(III) complex reversibly dissociates to the monomer Cp
670:
485:
to form the
Markovnikov alcohol and particularly axial cyclohexanols from
3760:
3626:
2736:
1410:
1079:
559:
The reagent has been used in the synthesis of over 20 natural products.
516:
331:
1585:
Keglevich, Péter; Hazai, Laszlo; Kalaus, György; Szåntay, Csaba (2012).
1336:
1247:
1218:
1147:
1118:
930:
896:
3852:
1306:
1296:
790:
589:
L. is the source for a number of important natural products, including
524:
452:
364:
309:
107:
2071:
2033:
1922:
1881:
1784:
1744:
1690:
1458:
1177:
647:
551:
439:
319:
An example of an application of this reagent is in the preparation of
2088:
1959:
1851:
1587:"Modifications on the basic skeletons of vinblastine and vincristine"
538:
501:
567:
and its carbon skeleton is incorporated with the structures of both
243:
Except where otherwise noted, data are given for materials in their
709:
527:
is possible, as well as conjunctive intra-intermolecular variants.
397:
389:
297:
94:
86:
75:
351:
2953:
2092:
1551:
Botanical
Miracles: Chemistry of Plants That Changed the World
686:
Bis(cyclopentadienyl)titanium(III) chloride also effects both
394:
NugentâRajanBabu reagent synthesis and equilibrium in solution
380:
814:
Cyclopentadienyl
Complexes of Titanium(III) and Vanadium(III)
767:(1955). "The reduction of bis-cyclopentadienyl compounds".
492:
Reaction of the intermediate with a second equivalent of Cp
617:, all of which can be obtained from the plant. The newer
447:
Bis(cyclopentadienyl)titanium(III) chloride effects the
292:
In the presence of a suitable solvent that can act as a
1720:
1718:
143:
InChI=1S/2C5H5.ClH.Ti/c2*1-2-4-5-3-1;;/h2*1-5H;1H;/p-1
379:
chlorides, though in an appropriate solvent such as
2912:
2621:
2302:
2284:
2202:
2187:
2126:
1053:
1051:
1049:
1047:
1901:
1899:
1580:
1578:
1576:
1574:
876:
874:
812:Manzer, L. E.; Mintz, E. A.; Marks, T. J. (1982).
467:In the presence of hydrogen atom donors, such as
119:
1516:. Medicinal and Aromatic Plants. Vol. VI.
61:
1671:Faller, Bryan A.; Pandi, Trailokya N. (2011).
1545:Cooper, Raymond; Deakin, Jeffrey John (2016).
1070:. Topics in Current Chemistry. Vol. 279.
1016:Encyclopedia of Reagents for Organic Synthesis
477:, water, the intermediate is protonated to an
327:which can be prepared in three steps from the
172:dimer: c1ccc1.c1ccc1.Cl1Cl1.c1ccc1.c1ccc1
2965:
2104:
507:The radical intermediate can also be trapped
8:
1513:Biotechnology in Agriculture and Forestry 26
1502:Hirata, K.; Miyamoto, K.; Miura, Y. (1994).
17:Bis(cyclopentadienyl)titanium(III) chloride
263:Bis(cyclopentadienyl)titanium(III) chloride
2972:
2958:
2950:
2618:
2281:
2184:
2111:
2097:
2089:
1764:
1762:
667:are reduced to their respective alcohols.
575:. A regioselective epoxide opening and 5-
15:
1698:
1614:
1604:
1418:
1305:
1295:
991:
910:
908:
906:
2861:
2857:
2847:
2843:
2833:
2829:
2819:
2815:
2059:Journal of the American Chemical Society
1910:Journal of the American Chemical Society
1398:Journal of the American Chemical Society
1324:Journal of the American Chemical Society
1135:Journal of the American Chemical Society
1106:Journal of the American Chemical Society
884:Journal of the American Chemical Society
669:
406:The molecule has been measured to be an
2980:Salts and covalent derivatives of the
1476:Angewandte Chemie International Edition
1353:Angewandte Chemie International Edition
755:
410:with a J-coupling constant of -138 cm.
164:
139:
3002:
1014:Nugent, William A. (January 1, 2001).
942:
940:
3741:
1267:
1265:
1263:
1261:
1259:
1257:
1072:Springer Science & Business Media
979:European Journal of Organic Chemistry
951:European Journal of Organic Chemistry
146:Key: GCXNJJRCRJQDSV-UHFFFAOYSA-M
7:
2992:
1678:Clinical Medicine Insights: Oncology
1389:"Enantioselective cross-coupling of
1387:Zhao, Yang; Weix, Daniel J. (2015).
1009:
1007:
1005:
1003:
694:couplings of aldehydes and ketones.
346:It is commonly prepared by reducing
763:Birmingham, J. M.; Fischer, A. K.;
110:
1278:TiCl in natural product synthesis"
739:TiCl. This 15 electron species is
304:, the dimer separates and forms a
14:
342:It was first reported in 1955 by
820:. Vol. 21. pp. 84â86.
726:using a stoichiometric reductant
718:bond and allows regeneration of
421:, and has found applications in
211:
205:
199:
22:
247:(at 25 °C , 100 kPa).
1984:Chemistry â A European Journal
1732:Journal of Medicinal Chemistry
678:-type reaction catalysed by Cp
193:
167:monomer: c1ccc1.Cl.c1ccc1
1:
2285:Organotitanium(III) compounds
1823:10.1016/S0040-4039(02)02703-X
865:10.1016/S0040-4039(00)96822-9
511:when an appropriate acceptor
3936:One-electron reducing agents
2913:Organotitanium(IV) compounds
2188:Organotitanium(II) compounds
1869:Journal of Organic Chemistry
1547:"Africa's gift to the world"
1510:. In Bajaj, Y. P. S. (ed.).
1446:Journal of Organic Chemistry
1393:-epoxides with aryl halides"
1235:Journal of Organic Chemistry
1206:Journal of Organic Chemistry
1165:Journal of Organic Chemistry
625:is used in the treatment of
1283:Organic Chemistry Frontiers
523:with radicals derived from
387:with monomeric structures:
283:synthetic organic chemistry
3957:
3931:Cyclopentadienyl complexes
3743:
1274:"Recent applications of Cp
1203:-butylcyclohexene oxide".
1028:10.1002/047084289x.rn00294
826:10.1002/9780470132524.ch18
627:non-small-cell lung cancer
583:The Madagascan periwinkle
3004:
2989:
1606:10.3390/molecules17055893
563:is a naturally-occurring
483:lithium aluminium hydride
241:
180:
155:
130:
45:
35:
30:
21:
1729:and phomopsin hybrids".
1638:Raviña, Enrique (2011).
643:silver tetrafluoroborate
537:of opened epoxides with
436:Use in organic synthesis
427:organometallic chemistry
267:NugentâRajanBabu reagent
40:NugentâRajanBabu reagent
1947:Chemical Communications
1839:Chemical Communications
696:Barbier-type reactivity
621:chemotherapeutic agent
601:it produces from them:
338:Synthesis and structure
271:organotitanium compound
38:titanocene monochloride
1997:10.1002/chem.201100501
993:10.1002/ejoc.201500761
964:10.1002/ejoc.201500292
727:
683:
652:
645:to yield vinorelbine.
556:
444:
419:T. V. (Babu) RajanBabu
403:
395:
371:The molecule adopts a
325:chemotherapeutic agent
314:cyclopentadienyl anion
1648:John Wiley & Sons
1020:John Wiley & Sons
713:
673:
656:Additional reactivity
651:
555:
504:product is generated.
498:ÎČ-hydride elimination
443:
401:
393:
348:titanocene dichloride
296:("solv"), such as an
285:as a single electron
1650:. pp. 157â159.
1411:10.1021/jacs.5b01909
1080:10.1007/128_2007_130
639:trifluoroacetic acid
385:chemical equilibrium
306:chemical equilibrium
265:, also known as the
2028:(20): 11859â11866.
2021:Inorganic Chemistry
1810:Tetrahedron Letters
1506:Catharanthus roseus
1337:10.1021/ja00194a073
1248:10.1021/jo01278a005
1219:10.1021/jo01034a015
1148:10.1021/ja00082a021
1119:10.1021/ja00173a045
1064:Krische, Michael J.
931:10.1021/ic50173a015
918:Inorganic Chemistry
897:10.1021/ja00233a051
852:Tetrahedron Letters
818:Inorganic Syntheses
783:1955NW.....42Q..96B
770:Naturwissenschaften
586:Catharanthus roseus
329:naturally-occurring
229: g·mol
18:
2622:Titanate compounds
2120:Titanium compounds
1557:. pp. 46â51.
1297:10.1039/c3qo00024a
1074:. pp. 25â52.
791:10.1007/BF00617242
728:
684:
653:
557:
469:1,4-cyclohexadiene
445:
408:open shell singlet
404:
396:
344:Geoffrey Wilkinson
294:two-electron donor
273:which exists as a
251:Infobox references
16:
3913:
3912:
3907:
3906:
2982:cyclopentadienide
2947:
2946:
2943:
2942:
2298:
2297:
2198:
2197:
2072:10.1021/ja067054e
2034:10.1021/ic401403a
1991:(20): 5507â5510.
1954:(22): 2628â2629.
1923:10.1021/ja906083c
1882:10.1021/jo9005238
1785:10.1021/ol025560c
1745:10.1021/jm801064y
1691:10.4137/CMO.S5074
1640:"Vinca alkaloids"
1459:10.1021/jo951930h
1360:(17): 3206â3208.
1331:(12): 4525â4527.
1213:(11): 3185â3188.
1178:10.1021/jo016277e
1113:(17): 6408â6409.
958:(21): 4567â4591.
891:(25): 8561â8562.
859:(46): 5717â5718.
635:-bromosuccinimide
487:epoxycyclohexanes
415:William A. Nugent
373:dimeric structure
277:with the formula
259:Chemical compound
257:
256:
96:Interactive image
88:Interactive image
3948:
3941:Chloro complexes
2993:
2974:
2967:
2960:
2951:
2864:
2850:
2836:
2822:
2619:
2613:
2612:
2611:
2603:
2602:
2594:
2593:
2585:
2584:
2282:
2185:
2113:
2106:
2099:
2090:
2084:
2083:
2066:(5): 1359â1371.
2052:
2046:
2045:
2015:
2009:
2008:
1978:
1972:
1971:
1960:10.1039/B411173G
1941:
1935:
1934:
1903:
1894:
1893:
1876:(9): 3616â3619.
1862:
1856:
1855:
1852:10.1039/A608438I
1833:
1827:
1826:
1817:(5): 1079â1082.
1803:
1797:
1796:
1779:(7): 1151â1153.
1766:
1757:
1756:
1722:
1713:
1712:
1702:
1668:
1662:
1661:
1635:
1629:
1628:
1618:
1608:
1599:(5): 5893â5914.
1582:
1569:
1568:
1542:
1536:
1535:
1499:
1493:
1492:
1483:(1â2): 101â103.
1469:
1463:
1462:
1453:(6): 2095â2108.
1439:
1433:
1432:
1422:
1405:(9): 3237â3240.
1384:
1378:
1377:
1347:
1341:
1340:
1318:
1312:
1311:
1309:
1299:
1269:
1252:
1251:
1229:
1223:
1222:
1196:
1190:
1189:
1172:(8): 2566â2571.
1158:
1152:
1151:
1129:
1123:
1122:
1100:
1094:
1093:
1055:
1042:
1041:
1011:
998:
997:
995:
967:
944:
935:
934:
925:(7): 1645â1655.
912:
901:
900:
878:
869:
868:
846:
840:
839:
809:
803:
802:
760:
725:
717:
665:benzylic ketones
532:enantioselective
509:intramolecularly
449:anti-Markovnikov
228:
213:
207:
201:
195:
188:Chemical formula
123:
112:
98:
90:
65:
26:
19:
3956:
3955:
3951:
3950:
3949:
3947:
3946:
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3916:
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3909:
3908:
3872:
3861:
3857:
3856:
3840:
3832:
3824:
3813:
3796:
3788:
3780:
3772:
3764:
3756:
3706:
3660:
3638:
3630:
3621:
3613:
3609:
3598:
3594:
3586:
3555:
3535:
3531:
3523:
3514:
3510:
3505:
3502:
3498:
3492:
3490:
3478:
3474:
3469:
3467:
3463:
3457:
3455:
3451:
3443:
3439:
3429:
3423:
3421:
3417:
3409:
3405:
3401:
3355:
3353:
3344:
3338:
3336:
3326:
3321:
3319:
3315:
3310:
3308:
3304:
3300:
3296:
3292:
3288:
3283:
3281:
3277:
3273:
3269:
3265:
3260:
3258:
3254:
3250:
3244:
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3213:
3204:
3199:
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3188:
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3181:
3172:
3168:
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3157:
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3141:
3139:
3134:
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3128:
3122:
3120:
3116:
3108:
3098:
3063:
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3039:
3035:
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2978:
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2896:
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2872:
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2849:
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2792:
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1980:
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1943:
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1864:
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1859:
1835:
1834:
1830:
1805:
1804:
1800:
1772:Organic Letters
1768:
1767:
1760:
1727:Vinca alkaloids
1724:
1723:
1716:
1670:
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1658:
1637:
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1518:Springer-Verlag
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806:
762:
761:
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738:
733:
723:
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706:
681:
658:
599:vinca alkaloids
495:
438:
432:
340:
302:tetrahydrofuran
280:
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79:
68:
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12:
11:
5:
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3700:
3697:
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3649:
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3640:
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3628:
3624:
3619:
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3607:
3603:
3600:
3596:
3592:
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3500:
3496:
3488:
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3411:
3407:
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3399:
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3379:
3376:
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3324:
3317:
3313:
3306:
3302:
3298:
3294:
3290:
3286:
3279:
3275:
3271:
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3263:
3256:
3252:
3248:
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3223:
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3207:
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3195:
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3179:
3175:
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3166:
3159:
3155:
3148:
3144:
3137:
3130:
3126:
3118:
3114:
3110:
3106:
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3096:
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3049:
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3018:
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3009:
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2991:
2990:
2987:
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2806:
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2726:
2722:
2718:
2714:
2710:
2706:
2702:
2698:
2694:
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2682:
2678:
2674:
2670:
2666:
2662:
2658:
2654:
2650:
2646:
2642:
2638:
2634:
2630:
2625:
2623:
2616:
2615:
2608:
2599:
2590:
2581:
2573:
2569:
2565:
2561:
2557:
2553:
2549:
2545:
2541:
2537:
2533:
2529:
2525:
2521:
2517:
2513:
2509:
2505:
2501:
2497:
2493:
2489:
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2433:
2429:
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2417:
2413:
2409:
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2373:
2369:
2365:
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2357:
2353:
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2341:
2337:
2332:
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2323:
2319:
2315:
2311:
2306:
2304:
2300:
2299:
2296:
2295:
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2286:
2279:
2278:
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2270:
2266:
2262:
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2254:
2249:
2244:
2240:
2236:
2232:
2228:
2224:
2220:
2216:
2212:
2206:
2204:
2200:
2199:
2196:
2195:
2191:
2189:
2182:
2181:
2177:
2173:
2168:
2163:
2159:
2155:
2151:
2147:
2143:
2139:
2135:
2130:
2128:
2124:
2123:
2118:
2116:
2115:
2108:
2101:
2093:
2086:
2085:
2047:
2010:
1973:
1936:
1917:(1): 254â259.
1895:
1857:
1846:(5): 457â458.
1828:
1798:
1758:
1739:(1): 134â142.
1714:
1663:
1656:
1630:
1570:
1563:
1537:
1530:
1494:
1464:
1434:
1379:
1342:
1313:
1275:
1253:
1242:(3): 537â539.
1224:
1191:
1153:
1142:(3): 986â997.
1124:
1095:
1088:
1043:
1036:
999:
936:
902:
870:
841:
834:
804:
754:
752:
749:
736:
732:
729:
721:
704:
679:
657:
654:
619:semi-synthetic
573:merrilactone A
550:
549:
535:cross-coupling
528:
521:acrylonitriles
505:
493:
490:
489:is well known.
437:
434:
383:, exists in a
339:
336:
278:
258:
255:
254:
249:
245:standard state
242:
239:
238:
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231:
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224:
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128:
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103:
102:
100:
99:
91:
85:monomer:
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80:
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66:
58:
56:
51:
48:
47:
43:
42:
37:
33:
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28:
27:
13:
10:
9:
6:
4:
3:
2:
3953:
3942:
3939:
3937:
3934:
3932:
3929:
3927:
3924:
3923:
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3902:
3899:
3896:
3893:
3890:
3887:
3884:
3881:
3878:
3875:
3873:
3867:
3864:
3862:
3851:
3848:
3845:
3844:
3841:
3835:
3833:
3827:
3825:
3819:
3816:
3814:
3808:
3805:
3802:
3799:
3797:
3791:
3789:
3783:
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3775:
3773:
3767:
3765:
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3599:
3589:
3587:
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3575:
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3571:
3567:
3564:
3561:
3558:
3556:
3550:
3548:
3545:
3542:
3539:
3537:
3526:
3524:
3518:
3516:
3515:
3504:
3491:
3485:
3482:
3480:
3479:
3468:
3456:
3446:
3444:
3434:
3432:
3431:
3422:
3412:
3410:
3396:
3394:
3391:
3388:
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3383:
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3368:
3365:
3362:
3360:
3359:
3354:
3348:
3346:
3345:
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3320:
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3282:
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3140:
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3101:
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2741:
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2725:
2711:
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2687:
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2669:
2663:
2661:
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2645:
2635:
2633:
2627:
2626:
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2620:
2614:
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2237:
2235:
2229:
2227:
2221:
2219:
2213:
2211:
2208:
2207:
2205:
2203:Titanium(III)
2201:
2193:
2190:
2186:
2180:
2174:
2172:
2169:
2167:
2164:
2162:
2156:
2154:
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2146:
2140:
2138:
2132:
2131:
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2125:
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2100:
2095:
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2065:
2061:
2060:
2051:
2048:
2043:
2039:
2035:
2031:
2027:
2023:
2022:
2014:
2011:
2006:
2002:
1998:
1994:
1990:
1986:
1985:
1977:
1974:
1969:
1965:
1961:
1957:
1953:
1949:
1948:
1940:
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1932:
1928:
1924:
1920:
1916:
1912:
1911:
1902:
1900:
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1883:
1879:
1875:
1871:
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1861:
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1853:
1849:
1845:
1841:
1840:
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591:catharanthine
588:
587:
581:
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574:
570:
569:anislactone A
566:
565:sesquiterpene
562:
561:Ceratopicanol
554:
547:
546:electrophiles
544:
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536:
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25:
20:
3493:
3458:
3424:
3356:
3339:
3245:
3216:
3184:
3123:
3064:
2303:Titanium(IV)
2289:
2127:Titanium(II)
2063:
2057:
2050:
2025:
2019:
2013:
1988:
1982:
1976:
1951:
1945:
1939:
1914:
1908:
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1322:
1316:
1290:(1): 15â33.
1287:
1281:
1239:
1233:
1227:
1210:
1204:
1200:
1194:
1169:
1163:
1156:
1139:
1133:
1127:
1110:
1104:
1098:
1067:
1015:
986:(21): 4592.
983:
977:
955:
949:
922:
916:
888:
882:
856:
850:
844:
813:
807:
774:
768:
758:
741:Lewis acidic
734:
685:
659:
641:followed by
632:
607:chemotherapy
584:
582:
576:
558:
543:pseudohalide
473:
461:nitro groups
457:free radical
446:
431:
423:free radical
412:
405:
370:
363:
341:
318:
291:
266:
262:
261:
237:green solid
93:dimer:
46:Identifiers
36:Other names
3926:Titanocenes
2544:·20TiO
2536:NiO·Sb
1685:: 131â144.
1520:. pp.
1307:10481/47295
674:Example of
623:vinorelbine
615:vincristine
611:vinblastine
451:opening of
334:leurosine.
321:vinorelbine
234:Appearance
181:Properties
3920:Categories
3507:RuCp(MeCN)
2885:Pb(Zr,Ti)O
751:References
716:Ti–O
222:Molar mass
74:3D model (
53:CAS Number
3471:(MoCp(CO)
3218:(CrCp(CO)
2488:Ti(OCH(CH
1592:Molecules
1555:CRC Press
777:(4): 96.
731:Mechanism
603:leurosine
595:vindoline
517:acrylates
360:magnesium
356:manganese
287:reductant
269:, is the
121:101376209
63:1271-18-7
3606:(WCp(CO)
3495:RuCp(PPh
3341:CoCp(CO)
3323:FeCp(CO)
2080:17263420
2042:24112112
2005:21488110
1968:15543313
1931:20000601
1890:19334701
1793:11922805
1753:19072542
1709:21695100
1625:22609781
1429:25716775
1374:12207390
1186:11950302
799:44523847
605:and the
597:and the
525:epoxides
453:epoxides
377:bridging
332:alkaloid
3744:
3201:VCp(CO)
2729:EuBaTiO
1700:3117629
1616:6268133
1420:4415026
1066:(ed.).
779:Bibcode
745:radical
701:Michael
692:McMurry
688:Pinacol
676:Barbier
609:agents
479:alcohol
365:in situ
310:reagent
108:PubChem
3528:PdCp(C
3358:NiCpNO
3247:Fe(η-C
3136:TiCpCl
3066:MgCpBr
2689:CaZrTi
2528:KTiOPO
2504:Ti(OCH
2404:Ti(NMe
2348:Ti(ClO
2078:
2040:
2003:
1966:
1929:
1888:
1791:
1751:
1707:
1697:
1654:
1623:
1613:
1561:
1528:
1427:
1417:
1372:
1184:
1086:
1034:
832:
797:
661:Cyclic
539:halide
513:moiety
502:olefin
227:427.01
160:SMILES
31:Names
3270:)Fe(C
3186:VCpCh
3125:(TiCp
2901:ZnTiO
2893:SrTiO
2877:PbTiO
2869:NiTiO
2773:MnTiO
2737:FeTiO
2665:CaTiO
2629:BaTiO
2416:Ti(NO
2396:TiOSO
2331:TiS(S
1522:46â55
1062:. In
795:S2CID
455:to a
375:with
358:, or
350:with
300:like
298:ether
275:dimer
135:InChI
76:JSmol
3858:ThCp
3853:ThCp
3837:YbCp
3829:TmCp
3821:ErCp
3810:DyCp
3793:SmCp
3785:PmCp
3777:NdCp
3769:PrCp
3761:CeCp
3753:LaCp
3703:HsCp
3657:PbCp
3652:TlCp
3635:IrCp
3627:OsCp
3618:ReCp
3591:HfCp
3583:LuCp
3552:SnCp
3547:InCp
3520:RhCp
3487:RuCp
3460:MoCp
3448:MoCp
3436:NbCp
3426:ZrCp
3414:ZrCp
3350:NiCp
3333:CoCp
3312:FeCp
3239:FeCp
3231:MnCp
3210:CrCp
3165:TiCp
3158:(CO)
3154:TiCp
3143:TiCp
3113:TiCp
3105:ScCp
3095:CaCp
3058:MgCp
3053:NaCp
3024:CpMe
3013:LiCp
2673:CaCu
2577:Ti(C
2568:TiSi
2560:TiSe
2472:(OCH
2448:Ti(C
2340:TiCl
2318:TiBr
2223:TiCl
2215:TiBr
2210:TiAl
2176:TiSi
2150:TiBr
2134:TiCl
2076:PMID
2038:PMID
2001:PMID
1964:PMID
1952:2004
1927:PMID
1886:PMID
1844:1997
1789:PMID
1749:PMID
1705:PMID
1652:ISBN
1621:PMID
1559:ISBN
1526:ISBN
1425:PMID
1391:meso
1370:PMID
1182:PMID
1084:ISBN
1032:ISBN
984:2015
956:2015
830:ISBN
724:TiCl
690:and
682:TiCl
663:and
637:and
613:and
593:and
571:and
541:and
519:and
475:BuSH
425:and
417:and
352:zinc
323:, a
3903:No
3900:Md
3897:Fm
3894:Es
3891:Cf
3888:Bk
3885:Cm
3882:Am
3879:Pu
3876:Np
3869:UCp
3865:Pa
3849:Ac
3846:**
3817:Ho
3806:Tb
3803:Gd
3800:Eu
3737:Og
3734:Ts
3731:Lv
3728:Mc
3725:Fl
3722:Nh
3719:Cn
3716:Rg
3713:Ds
3710:Mt
3699:Bh
3696:Sg
3693:Db
3690:Rf
3687:Lr
3684:**
3681:Ra
3678:Fr
3673:Rn
3670:At
3667:Po
3664:Bi
3648:Hg
3645:Au
3642:Pt
3602:Ta
3576:Ba
3573:Cs
3568:Xe
3562:Te
3559:Sb
3543:Cd
3540:Ag
3483:Tc
3430:ClH
3398:Y(C
3392:Sr
3389:Rb
3384:Kr
3381:Br
3378:Se
3375:As
3372:Ge
3369:Ga
3366:Zn
3363:Cu
3262:((C
3255:Li)
3190:VCp
3178:VCp
3129:Cl)
3086:Ar
3083:Cl
3074:Si
3071:Al
3047:Ne
3017:Be
3007:He
2997:CpH
2984:ion
2860:TiF
2846:TiF
2832:TiF
2818:TiF
2805:TiO
2803:0.5
2799:0.5
2765:TiO
2705:TiO
2641:TiO
2552:TiS
2440:TiO
2428:TiO
2388:TiI
2380:TiH
2372:TiF
2360:TiF
2326:TiC
2310:TiB
2252:TiP
2247:TiN
2239:TiI
2231:TiF
2171:TiS
2166:TiO
2158:TiI
2142:TiH
2068:doi
2064:129
2030:doi
1993:doi
1956:doi
1919:doi
1915:132
1878:doi
1848:doi
1819:doi
1781:doi
1741:doi
1695:PMC
1687:doi
1611:PMC
1601:doi
1485:doi
1455:doi
1415:PMC
1407:doi
1403:137
1362:doi
1333:doi
1329:111
1302:hdl
1292:doi
1244:doi
1215:doi
1174:doi
1144:doi
1140:116
1115:doi
1111:112
1076:doi
1024:doi
988:doi
960:doi
927:doi
893:doi
889:110
861:doi
822:doi
787:doi
577:exo
381:THF
111:CID
3922::
3749:*
3595:Cl
3579:*
3565:I
3511:PF
3503:Cl
3464:Cl
3440:Cl
3418:Cl
3316:PF
3305:Fe
3293:-C
3285:(C
3278:))
3194:Cl
3169:Me
3117:Cl
3091:K
3080:S
3077:P
3044:F
3028:N
3020:B
2856:Rb
2842:Li
2814:Na
2801:Bi
2797:Na
2785:Ti
2781:Na
2761:Li
2749:Ti
2745:Ho
2717:Ti
2713:Dy
2701:Cs
2683:12
2677:Ti
2659:12
2653:Ti
2649:Bi
2637:Ba
2516:CH
2512:CH
2508:CH
2482:16
2476:CH
2468:Ti
2269:Ti
2257:Ti
2074:.
2062:.
2036:.
2026:52
2024:.
1999:.
1989:17
1987:.
1962:.
1950:.
1925:.
1913:.
1898:^
1884:.
1874:74
1872:.
1842:.
1815:44
1813:.
1787:.
1775:.
1761:^
1747:.
1737:52
1735:.
1717:^
1703:.
1693:.
1681:.
1675:.
1646:.
1642:.
1619:.
1609:.
1597:17
1595:.
1589:.
1573:^
1553:.
1549:.
1524:.
1481:37
1479:.
1451:61
1449:.
1423:.
1413:.
1401:.
1395:.
1368:.
1358:41
1356:.
1327:.
1300:.
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1280:.
1256:^
1240:32
1238:.
1211:29
1209:.
1180:.
1170:67
1168:.
1138:.
1109:.
1082:.
1046:^
1030:.
1022:.
1018:.
1002:^
982:.
976:.
954:.
939:^
923:16
921:.
905:^
887:.
873:^
857:28
855:.
828:.
816:.
793:.
785:.
775:42
773:.
720:Cp
471:,
429:.
368:.
354:,
316:.
289:.
212:Ti
206:Cl
203:20
197:20
3871:4
3860:4
3855:3
3839:3
3831:3
3823:3
3812:3
3795:3
3787:3
3779:3
3771:3
3763:3
3755:3
3705:2
3659:2
3637:2
3629:2
3622:H
3620:2
3612:2
3610:)
3608:3
3597:2
3593:2
3585:3
3554:2
3536:)
3534:5
3532:H
3530:3
3522:2
3513:6
3509:3
3501:2
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3497:3
3489:2
3477:2
3475:)
3473:3
3466:2
3462:2
3454:2
3452:H
3450:2
3442:2
3438:2
3428:2
3420:2
3416:2
3408:3
3406:)
3404:5
3402:H
3400:5
3352:2
3343:2
3335:2
3327:I
3325:2
3318:6
3314:2
3307:2
3303:2
3301:)
3299:4
3297:H
3295:5
3291:4
3289:H
3287:5
3280:2
3276:4
3274:H
3272:5
3268:5
3266:H
3264:5
3257:2
3253:4
3251:H
3249:5
3241:2
3233:2
3224:2
3222:)
3220:3
3212:2
3203:4
3196:2
3192:2
3180:2
3171:2
3167:2
3160:2
3156:2
3149:5
3147:S
3145:2
3138:3
3131:2
3127:2
3119:2
3115:2
3107:3
3097:2
3060:2
3040:O
3038:4
3036:H
3034:5
3032:C
2973:e
2966:t
2959:v
2903:3
2895:3
2887:3
2879:3
2871:3
2862:6
2858:2
2848:6
2844:2
2834:6
2830:2
2828:K
2820:6
2816:2
2807:3
2791:7
2789:O
2787:3
2783:2
2775:3
2767:3
2763:2
2755:7
2753:O
2751:2
2747:2
2739:3
2731:4
2723:7
2721:O
2719:2
2715:2
2707:3
2703:2
2695:7
2693:O
2691:2
2681:O
2679:4
2675:3
2667:3
2657:O
2655:3
2651:4
2643:4
2639:2
2631:3
2609:4
2604:)
2600:3
2595:O
2591:5
2586:H
2582:3
2570:2
2562:2
2554:2
2546:2
2542:3
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2530:4
2522:4
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2518:3
2514:2
2510:2
2506:2
2498:4
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2490:3
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2478:3
2474:2
2470:4
2462:4
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2442:4
2438:4
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2422:4
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2410:4
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2390:4
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2374:6
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2342:4
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2333:2
2320:4
2312:2
2291:2
2275:3
2273:S
2271:2
2263:3
2261:O
2259:2
2241:3
2233:3
2225:3
2217:3
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1970:.
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548:.
494:2
279:2
215:2
209:2
200:H
194:C
78:)
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