Regioselective Preparation of Allylgermanes

Article abstract of DOI:10.1246/bcsj.66.607

Allylgermanes were obtained by the reaction of allyl acetates with bis(triethylgermyl)cuprate(I) reagent in high yields.It was found that the present reaction proceeded with high regioselectivity, in which a triethylgermyl group was exclusively introduced to the less substituted side of an allylic system regardless of the original location of acetoxyl group.In the case of the allyl acetates possessing two secondary centers at the both ends of the allylic system, the formal S_N2 product was preferentially produced (S_N2:S_N2'=ca. 9:1).The desulfurizative germylation of allyl phenyl sulfides utilizing bis(triethylgermyl)cuprate(I) reagent also proceeded to give allylgermanes in good yields with the same regioselectivity.