No 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 CHCl3 and in AcOH, and product distributions were studied. The results suggest that the loss of N2 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-center two-electron bonding, while the loss of N2 from a secondary alkanediazonium ion occurs spontaneously to form a secondary carbocation. Solvent effects (CHCl3 vs AcOH) are explained in terms of lower nucleophilicity/basicity of the AcO− in AcOH than in CHCl3 due to solvation.

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Deamination of 1-Alkyl-9-aminomethyltriptycenes. Participation of a Neighboring 1-Alkyl Substituent. -In continuation of an earlier research, the deamination reaction of products such as (I), (VI) and (VIII) is investigated. The mechanistical aspects are discussed in detail. -(YAMAMOTO*, G.; KOSEKI, A.; SUGITA, J.; MOCHIDA, H.; MINOURA, M.; Bull. Chem.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.