Reduction of aryltrimethylsilanes as a synthetic method. Part II. Birch reduction

Abstract

Sixteen aryltrimethylsilanes have been reduced by a modification of the Birch reduction (with lithium–ethanol; lithium added last). Along with the expected cyclohexa-1,4-dienes, products of Si–C bond cleavage are also formed, especially when an allylic or benzylic Si–C bond is involved; further reduction to substituted cyclohexenes or cyclohexanes may take place if the primary product contains vinylic trimethylsilyl groups.