Conversion of 2,5-dimethylfuran in to 2-benzyl-5-methylfuran by N-nitrosoacetanilide: an unprecedented aromatic side-chain phenylation

Abstract

Decomposition of N-nitrosoacetanilide in a mixture of 2,5-dimethylfuran and benzene at room temperature gave biphenyl, formed via phenyl radicals, and 2-benzyl-5-methylfuran formed, it is suggested via a novel deprotonation by acetate ion of a dimethylfuran-benzenediazonium cation complex, the expected radical-derived products from 2,5-dimethylfuran being absent.