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Communication | Regular issue | Vol 29, No. 4, 1989, pp.649-651
Published online, 1st January, 1970
DOI: 10.3987/COM-89-4864
Strained Heterocyclic Systems. 16. 1-Azatriotycene

J. Hodge Markgraf,* Kathryn J. Leonard, Marlene E. Morrison, and Christopher R. Myers

*Department of Chemistry, Williams College, 47 Lab Campus Drive, Williamstown, MA 01267, U.S.A.

Abstract

The first synthesis of 1-azatriptycene (1) was accomplished in four steps from 2-naphtnylamine. Its pkα was determined by potentiometric titration and compared to that of diphenyl-2-pyridylmethane. The seven-fold decrease in the basicity of 1 was attributed to ring strain effects.