SYNTHESIS OF MONO-FLUORINATED QUINONES BY AN UNUSUAL S(RN)1 REACTION - DIFLUOROMETHYL QUINONES AS SUBSTRATES

Aldehydes are transformed into stable gem-difluoro compounds. Upon sta ndard S(RN)1 reaction conditions, they generate anion radicals that un dergo a very fast fluoride elimination to produce methylene quinones w hich are alkylated by a nucleophile. This process gives rise to facile access to new fluorinated species having any side chain. It is the fi rst reported example of gem-difluoro compounds reacting by the S(RN)1 mechanism.