REARRANGEMENT STUDIES WITH C¹⁴: XVI. REARRANGEMENTS INDUCED BY γ -IRRADIATION OF 2-PHENYLETHYL-1-C¹⁴ BROMIDE OR 2-p-METHOXYPHENYLETHYL-1-C¹⁴ BROMIDE

Abstract

Irradiation of 2-phenylethyl-1-C14 bromide with up to 133 million rads of Co60 y-rays gave 2-phenylethyl-2-C14 bromide with a mean G, of 0 . 3 0 f 0.01. Similar studies with 2-p-methoxyphenylethyl-1-C14 bromide resulted in 2-p-methoxyphenylethyl-2-C14 bromide with a mean G, of 0.46+0.04. Monomeric, liquid organic products were found to be benzene, ethylbenzene, and styrene, or the analogous p-methoxy derivatives, from the irradiation of 2-phenylethyl bromide or 2-p-methoxyphenylethyl bromide, respectively. Possible mechanisms for the radiationinduced isotope position rearrangements are discussed.

Rearrangement Studies with 14C. XXXVI. Solvolysis of 1-14C-2-Phenylethyl Tosylate in Aqueous Acetic Acid with or without Added Sodium Azide

“…The 1-OTs-14C recovered from the solvolysis in H,O was converted to 1-Br-I4C by treatment with LiBr in dry acetone (14). The 1-Br-14C so obtained was also oxidized to benzoic acid (9) in order to ascertain the extent of rearrangement.…”