Deamination of 1-alkyl-9-aminomethyltriptycenes. Participation of a neighboring 1-alkyl substituent

G Yamamoto, A Koseki, J Sugita, H Mochida…

Index: Yamamoto, Gaku; Koseki, Ai; Sugita, Jun; Mochida, Hisashi; Minoura, Mao Bulletin of the Chemical Society of Japan, 2006 , vol. 79, # 10 p. 1585 - 1600

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Citation Number: 5

Abstract

Deamination reactions of 1-alkyl-9-aminomethyltriptycenes (alkyl= Me, Et, i-Pr, and t-Bu) and 9-(1-aminoethyl)-1-methyltriptycene were performed in CHCl 3 and in AcOH, and product distributions were studied. The results suggest that the loss of N 2 from a primary alkanediazonium ion predominantly takes place concomitantly with participation of a C–H bond of the neighboring 1-alkyl group to form a nonclassical cationic species with a three- ...