The 2,4,6-trimethylbenzyltrimethylammonium ion was found to undergo with sodium amide in liquid ammonia the first phase of the ortho substitution rearrangement to give an e*o-methylenecyclohexadieneamine. This al ¡cyclic compound underwent thermal isomerization to form /3-mesitylethyldimethylamine, and reacted with electrophilic and nucleophilic reagents to produce certain aromatic compounds and by-products. The latter reagents formed an intermediate alicyclic product. Mechanisms for these reactions are discussed. The exo-methyleneamine also was hydrogenated.
The exo-methylenecyclohexadieneamine obtained from the rearrangement of the 2,4,6-trimethylbenzyltrimethylammonium ion by means of sodium amide in liquid ammonia was converted to another exo-methyleneamine by further treatment of its methiodide with this reagent. Like the former exo-methyleneamine, the latter aiicyclic product underwent thermal isomerization to a /3-arylethylamine, and an acid-induced decomposition to form an aromatic hydrocarbon. The mechanism for the conversion of the first exo-methyleneamine to the second is presented. Still further rearrangements are considered.
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