Preparation of aromatic nitro-compounds through nitrosodestannylation. 1,2-dihydro-3-nitrobenzocyclobutene and trimethyl-p-nitrophenylstannane

Abstract

Cleavage of aryltrimethylstannanes by nitrosyl chloride followed by oxidation of the resulting nitroso-compound has been shown to provide a useful route to some aromatic nitro-compounds. The method is illustrated by the preparation of 1,2-dihydro-3-nitrobenzocyclobutene (‘3-nitrobenzocyclobutene’) from 1,2-dihydro-3-trimethyl-stannylbenzocyclobutene and of trimethyl-p-nitrophenylstannane from p-bis(trimethylstannyl)benzene.