Transmetalation and Double Metal Exchange: A Convenient Route 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)