By Manfred Schlosser
Chapter I Organoalkali Chemistry (pages 1–352): Manfred Schlosser
Chapter II Organotin Chemistry (pages 353–464): James A. Marshall
Chapter III Organoboron Chemistry (pages 465–533): Keith Smith
Chapter IV Organoaluminum Chemistry (pages 535–577): Hisashi Yamamoto
Chapter V Organozinc Chemistry (pages 579–664): Eiichi Nakamura
Chapter VI Organocopper Chemistry (pages 665–815): Bruce H. Lipshutz
Chapter VII Organotitanium Chemistry (pages 817–923): Manfred T. Reetz
Chapter VIII Organozirconium Chemistry (pages 925–1002): Ei?Ichi Negishi
Chapter IX Organoiron and Organochromium Chemistry (pages 1003–1121): Martin F. Semmelhack
Chapter X Organopalladium Chemistry (pages 1123–1217): Louis S. Hegedus
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Extra info for Organometallics in Synthesis A Manual
Magnesium reacts with anthracene in tetrahydrofuran solution to form the ‘dianion’ 9,10-magnesia-9,10-dihydroanthracene (93)[370,371] . g. 94 or 95)[372 – 379] , but 1 : 2 adducts (‘dianions’) only under exceptional circumstances[380 – 382] . Mg 93 Na Li 94 95 Lithium, sodium or calcium dissolved in ammonia or alkylamines can reversibly generate radical anions even with benzene. These species may be trapped in situ with proton sources such as water, methanol, ethanol or tert-butyl alcohol .
Hoppe and his collaborators[311 – 315] . [316,317] discovered a major extension when they succeeded in the enantioselective ˛-lithiation of N-(tert-butoxycarbonyl)pyrrolidine. ) of 88–99%. R CH2 R C N O O R = alkyl, 1-alkenyl, aryl N C OC(CH3)3 O R C O C N O Li H O SPA 77 N C OC(CH3)3 O Li H SPA 78 The survey of the conﬁgurational stability of ˛-oxy- and ˛-amino-substituted organolithium species given below (see Fig. 7) should be taken as only qualitatively valid. Despite the approximations made, distinct trends can be recognized.
M S D THF (%) S D MEGME (%) Li Na K Cs 80 5 0 0 100 95 10 0 Nuclear magnetic resonance represents another technique with which to probe structural reorganizations of organometallic species. When the latter are ‘titrated’ with up to 10 equivalents of hexamethylphosphoric triamide (HMPA), one can differentiate three model cases. Tight aggregates such as methyllithium tetramer do not disintegrate but get peripherally solvated by the polar additive . 9-Fluorenyllithium[168,169] , triphenylmethyllithium and lithium triphenylmercurate , which exist exclusively as ion pairs at low temperatures ( 120 to 130 ° C) and in THF-rich media, progressively replace all four THF molecules in the ﬁrst coordination sphere of the lithium cation by HMPA.