Ortho Substitution Rearrangement of Certain 3-Substituted and 3, 5-Disubstituted Benzyltrimethylammonium Ions by Sodium Amide1

WQ BEARD Jr, DNVAN EENAM…

Index: Beard,W.Q. et al. Journal of Organic Chemistry, 1961 , vol. 26, p. 2310 - 2316

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Citation Number: 22

Abstract

The 3-methoxy-, 3-methyl-, and 3-chloro-benzyltrimethylammonium ions underwent the ortho substitution rearrangement Kith sodium amide in liquid ammonia to form mixtures of the two possible types of isomeric amines in yields of 92, 90, and l67@, respectively. With the first two quaternary ions, rearrangement into the ortho position versus the para position occurred in the ratio of 2: 1 and 1.2: 1, respectively. The 3-bromo and 3-trifluoromethyl ...