Compatible as a textbook for a graduate seminar in mathematical modelling, and as a source for scientists in quite a lot of disciplines. provides 22 lectures from a global convention in Leibnitz, Austria (no date mentioned), explaining fresh advancements and ends up in differential equatio
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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.