REARRANGEMENT STUDIES WITH C14: II. THE PREPARATION OF 2-PHENYLETHYL HALIDES

Abstract

The 2-phenylethyl halides were prepared from the treatment of 2-phenylethanol-1-C14 with thionyl chloride alone, thionyl chloride in pyridine, 48% hydrobromic acid, 55% hydroiodic acid, or phosphorus and iodine. Except for the reaction with thionyl chloride in pyridine, these reactions gave rise to some rearrangement of the C14 activity from the C-1 to the C-2 position. It appears probable that these rearrangements resulted from reactions having the SN1 type of mechanism with the phenylethyl cation as reaction intermediate. The fact that the thionyl chloride in pyridine treatment leads to a product without rearrangement is of interest in that this method may have further applications in synthetic tracer chemistry.