Selectivity in allylic substitutions with organometallics through neighbouring co-ordination. Part 2. Reactions of 2-allylthiobenzothiazoles with organocopper reagents

Abstract

Efficient control of the regioselectivity in allylic substitutions with Grignard reagents in the presence of copper(I) bromide has been achieved by using 2-allylthiobenzothiazoles as electrophiles. The S_N2:S_N2′ product ratio depends on the degree of co-ordination between the allylic reagent and the organometallic species.