Rearrangement of 2, 4, 6-Trimethylbenzyltrimethylammonium Ion by Sodium Amide to Form an exo-Methylenecyclohexadieneamine and its Reactions1

CR Hauser, DN Van Eenam

Index: Hauser; Van Eenam Journal of the American Chemical Society, 1957 , vol. 79, p. 5512,5518

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Citation Number: 34

Abstract

The 2, 4, 6-trimethylbenzyltrimethylammonium ion was found to undergo with sodium amide in liquid ammonia the first phase of the ovtho substitution rearrangement to give an exo- methylen~ cyclohesadieneamine. This alicyclic compound underwent thermal isomerization to form &mesitylethyldimethylamine, and reacted with electrophilic and nucleophilic reagents to produce certain aromatic compounds and by-products. The latter reagents ...