The Migration Aptitude of Benzyl vs. Methyl in Carbonium Ion Reactions of the 2, 2-Dimethyl-3-phenyl-1-propyl System

P Warrick, WH Saunders

Index: Warrick,P.; Saunders,W.H. Journal of the American Chemical Society, 1962 , vol. 84, p. 4095 - 4100

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Citation Number: 12

Abstract

The rearrangement of 2, 2-dimethyl-3-phenyl-l-propyl P-toluenesulfonate (Ia) by refluxing in formic acid and in acetic acid and of 2, 2-dimethyl-3-phenyl-l-propylamine(Ib) by treatment with sodium nitrite in acetic acid yielded mixtures of olefins and esters. The mixtures, after treatment with lithium aluminum hydride, were analyzed by gas chromatography and infrared and ultraviolet spectroscopy. Migration aptitudes of methyl/benzyl of 3.5, 3.2 and ...