Alkylation of bromocyclopropanes and bromoarenes by means of dibutylcopperlithium and alkyl halides.

T Hiyama, H Yamamoto, K Nishio, K Kitatani…

Index: Hiyama,T. et al. Bulletin of the Chemical Society of Japan, 1979 , vol. 52, p. 3632 - 3637

Full Text: HTML

Citation Number: 18

Abstract

Treatment of bromocyclopropanes with excess dibutylcopperlithium in tetrahydrofuran at− 48° C gives the respective organocopper intermediates which upon quenching with excess alkyl halides afford alkylated cyclo-propanes with retention of the configuration. This process is applied to the synthesis of methyl cascarillate. Bromoarenes are also reduced with dibutylcopperlithium and allylarenes are prepared therefrom.