REARRANGEMENT STUDIES WITH C14: XIV. THE REACTION OF 2-p-ANISYLETHANOL-1-C14 WITH THIONYL CHLORIDE

Abstract

Reaction between 2-p-anisylethanol-1-C14 and thionyl chloride was carried out with pyridine, n-hexane, toluene, dioxane, or excess thionyl chloride as solvent. The 2-p-anisylethyl chloride obtained showed rearrangement of the C14 label from the C-1 to C-2 positions ranging from about 0.5% for the reaction in pyridine to about 46% for the reaction in excess thionyl chloride. The results can be explained on the basis of varying degrees of involvement of the ethylene-p-methoxyphenonium chlorosulphite ion pair, thus supporting the suggestion that thermal decomposition of alkyl chlorosulphites to give chlorides may be considerably ionic in character.