Transmetalation and double metal exchange. Convenient way to organolithium compounds of the benzyl and allyl type

Treating PhMe with BuLi in the presence of KOCMe3 gave PhCH2K, which on LiBr treatment was converted into 85% PhCH2Li, characterized with Me3SiCl as PhCH2SiMe3. Similarly, at -20 Deg H2C:CMe2 gave 80% H2C:CMeCH2Li converted by CO2 or ethylene oxide into H2C:CMeCH2CO2H or H2C:CMe(CH2)3OH, resp. The similarly prepd. 2-C10H7CH2M (C10H7 = naphthyl; M = K, Li (I)] were obtained only with LiOCMe3 impurities due to their soly. I was characterized by carboxylation yielding 2-naphthaleneacetic acid. [on SciFinder (R)]

Published in:
Angewandte Chemie, International Edition, 12, 508-509
CAN 79:92315 29-2 Organometallic and Organometalloidal Compounds Inst. Chim. Org.,Univ. Lausanne,Lausanne,Switz. Journal 0044-8249 written in German. 36456-31-2 Role: RCT (Reactant), RACT (Reactant or reagent) (lithiation of); 91-57-6; 108-88-3; 115-11-7 Role: RCT (Reactant), RACT (Reactant or reagent) (metalation of); 2785-29-7P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and lithiation of); 581-96-4P; 766-04-1P; 1617-31-8P; 22508-64-1P; 36456-32-3P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of); 29917-94-0P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn., carboxylation and reaction with ethyloxirane)

 Record created 2006-03-03, last modified 2018-12-03

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