Synthesis of Mono-Fluorinated Quinones by an Unusual SRN1 Reaction: Difluoromethyl Quinones as Substrates

Abstract

Aldehydes are transformed into stable gem-difluoro compounds. Upon standard SRN1 reaction conditions, they generate anion radicals that undergo a very fast fluoride elimination to produce methylene quinones which are alkylated by a nucleophile. This process gives rise to facile access to new fluorinated species having any side chain. It is the first reported example of gem-difluoro compounds reacting by the SRN1 mechanism.