The Ortho Substitution Rearrangement versus β-Elimination of Certain Quaternary Ammonium Ions with Sodium Amide. Extension of the Method of Synthesis of …

CR Hauser, AJ Weinheimer

Index: Hauser; Weinheimer Journal of the American Chemical Society, 1954 , vol. 76, p. 1264,1266

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Citation Number: 6

Abstract

Certain benzyl quaternary ammonium ions having both methyl and higher alkyl groups were found to undergo, with sodium amide in liquid ammonia, both the ortho substitution rearrangement and p-elimination. Quaternary ammonium ion I11 underwent largely p- elimination, but quaternary ions V and VI1 exhibited more of the rearrangement than p- elimination. The latter ion formed on rearrangement the ortho ethyl derivative (VIII), the ...