REARRANGEMENT STUDIES WITH C14: XVII. A REINVESTIGATION OF THE REACTION OF 2-PHENYLETHYL-1-C14 BROMIDE WITH MAGNESIUM AND COBALTOUS BROMIDE IN REFLUXING ETHER

Abstract

Treatment of 2-phenylethyl-1-C14 bromide with magnesium and cobaltous bromide in refluxing ether gave ethylbenzene and styrene with no isotope position rearrangement. The results are contrary to those reported by Smith and Anderson. It was also found that oxidation of styrene-β-C14 with concentrated nitric acid gave p-nitrobenzoic acid containing 3–4% of the original styrene activity. Nitric acid oxidation of "regenerated styrene" from labeled styrene dibromide under different conditions gave 5.7–37.8% rearrangement. The mechanistic implications of the experimental results are discussed.