The Metal - Carbon Bond: Volume 4 (1987)

Chapter 1 training and use in natural synthesis of organolithium and workforce IA organometallics (pages 1–157): J. L. Wardell
Chapter 2 instruction and use of Grignard and workforce II organometallics in natural synthesis (pages 159–306): C. L. Raston and G. Salem
Chapter three training and use of organoboranes in natural synthesis (pages 307–409): D. S. Matteson
Chapter four training and use of organoaluminium compounds in natural synthesis (pages 411–472): P. A. Chaloner
Chapter five training and use of organothallium (III) compounds in natural synthesis (pages 473–538): S. Uemura
Chapter 6 training and use of organosilicon compounds in natural synthesis (pages 539–622): E. W. Colvin
Chapter 7 Use of organoiron compounds in natural synthesis (pages 623–732): Didier Astruc
Chapter eight Use of organorhodium compounds in natural synthesis (pages 733–818): F. H. Jardine
Chapter nine Use of organonickel compounds in natural synthesis (pages 819–888): ok. Tamao and M. Kumada
Chapter 10 Transition metal?stabilized carbocations in natural synthesis (pages 889–978): A. J. Pearson
Chapter eleven Hydrogenation (pages 979–1048): D. Parker
Chapter 12 Mechanism of homogeneous hydrogenation (pages 1049–1072): F. H. Jardine
Chapter thirteen Saturated carbon—hydrogen bond activation (pages 1073–1162): J. R. Chipperfield and D. E. Webster
Chapter 14 Supported steel complicated catalysts (pages 1163–1226): F. R. Hartley

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Extra resources for The Metal - Carbon Bond: Volume 4 (1987)

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Tmed, hexane, - 20 "C BuLI, thf, hexane or NaNH,, liq. NH, or KNH,, liq. ), thf, hexane, 0 "C CH2Li & CH2Li 771 772 173 714 qcH2L (90) 6-6 CH2Li 115 CH2Li (93) 776 39 1. Organic Synthesis of Organolithium TABLE 7. ) wMe Compound wMe a"':b Product (yield, %) Conditions BuLi, thf, hexane (75) NaNH,, liq. NH, (42) LiNPr',, thf, hexane (69) Me Ref. ), thf, hexane PhCH(CN)OSiMe, LiNPr',, thf, - 78 "C OSiMe3 I PhC-P(OEt)2 II I Li 0 (el) 786 (88) 787 PhCHLiCN (95) PhCHLi2CN (81) 788 789 CN I PhCOSil\le3 790 Li (90) J.

5-7and Their Arene Radical Anions or Dianion Compounds l4 I 4 2 Formation of organoalkali metal compounds by metallation of organic compounds using the metals has only been profitably achieved with the more acidic hydrocarbons, such as Ph,CH,-, ( n = l-3), fluorene, indene, cyclopentadiene, and alk-I-ynes, in a variety of solvents including ethers, hydrocarbons, and liquid ammonia. In the last medium, the formation of amides, MNH,, occurs and metallations proceed via these species'. The ease of metallation of phenylmethanes, Ph,CH,-,, at benzylic sites by metals follows the acidity sequence, namely Ph,CH > Ph,CH, > PhCH,.

Metallation of p-xylenes by BuLi-tmed or C,H, ,Na-tmed produces p MCH,C,H,Me but not p-(MCH,),C,H, (30, M = Li or Na); however, 30 (M = K) can be produced from the more powerful metallating agent BuLi-Bu'OK. An explanation for the xylene results has been based on the relative charges delocalized into the ring of the benzyl anion: the magnitudes decrease in the sequence p- > o- > m-, which is the reverse of the reactivities towards metallation. e. m- > o- and p; the easier formation of o-(MCH,),C,H, compared with p-(MCH,),C,H, is considered to be due to the lone pair attractive interactions between adjacent benzylic sites.

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