Preparation and chemistry of some 1-Iodo-1-phenylpropenes

Abstract

The oxidation of eight aryl alkyl hydrazones with iodine in the presence of triethylamine gave mixtures of 1-iodo-1-arylpropenes and ketones in yields of 36-73% and 19-43% respectively. Further evidence is presented in favour of an iodocarbonium ion intermediate for this reaction. Aspects of the photochemistry of 1-iodo-1-arylpropenes and their reaction with naphthylsodium are reported. The product distribution of the naphthylsodium reactions is consistent with an intermediate sp²-hybridized (?bent?) 1-arylpropenyl radical.