Oxidation of hydrazones with iodine in the presence of base

Abstract

The oxidation of 14 hydrazones with iodine in the presence of base (generally triethylamine) was investigated. The typical reaction products are mixtures of gem-diiodides and vinyl iodides obtained in total yields of 38-85%. The features of the reaction are consistent with a mechanism involving an intermediate iododiazonium salt and/or an iodocarbonium ion. The preparation and purification of hydrazones was investigated.