The Journal of Organic Chemistry

Competing hydride transfer and ene reactions in the aminoalkylation of 1-alkenes with N, N-dimethylmethyleniminium ions. A literature correction

T Cohen, A Onopchenko

Index: Cohen, Theodore; Onopchenko, Anatoli Journal of Organic Chemistry, 1983 , vol. 48, # 24 p. 4531 - 4537

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Citation Number: 12

Abstract

A literature report that NJV-dimethylmethyleniminium ion (2) reacts with propylene and styrene to form unsaturated tertiary amines is shown to be incorrect. The major products are the secondary amines 1-(methy1amino) butane and l-(methylamin0)-3-phenylpropane in which N-demethylation has occurred along with the saturation of the alkene. Analogous major products are formed with 1-butene, 1-hexene, 1-octene, 1-dodecene, 1-tetradecene ...