The Journal of Organic Chemistry

Symmetrically trisubstituted triptycenes

ME Rogers, BA Averill

Index: Rogers, Miriam E.; Averill, Bruce A. Journal of Organic Chemistry, 1986 , vol. 51, # 17 p. 3308 - 3314

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Citation Number: 33

Abstract

A simple synthesis of 1, 8, 13-and 1, 8, 16-trisubstituted triptycenes is described. Diels-Alder reaction of l, &disubstituted anthracenes with ortho-substituted benzynes gave 15 new triptycene compounds as mixtures of the syn (1, 8, 13) and anti (1, 8, 16) trisubstituted triptycenes, which in most cases could be separated by HPLC to afford pure isomeric products. The syn/anti ratio depends on the nature of the substituents on the anthracene ...