CHEMISTRY OF TRIVALENT IODINE-III THE ACTION OF IODOBENZENE DICHLORIDE ON PRIMARY ALCOHOLS AND ALDEHYDES

Article abstract of DOI:10.1016/S0040-4020(01)91882-4

Iodobenzene dichloride reacts with saturated primary alcohols at room temperature in the presence of pyridine to give esters and acid chlorides.With the corresponding aldehydes, only the latter type of product is obtained.While pivaldehyde raects normally, benzaldehyde is unaffected by the reagent under the same conditions.Presence of moisture results in formation of acids.It is suggested that reactions of both types of substrates involve base catalysed fragmentation of iodonium intermediates.