Rational tetraarylporphyrin syntheses: tetraarylporphyrins from the MacDonald route

DM Wallace, SH Leung, MO Senge…

Index: Wallace, David M.; Leung, Sam H.; Senge, Mathias O.; Smith, Kevin M. Journal of Organic Chemistry, 1993 , vol. 58, # 25 p. 7245 - 7257

Full Text: HTML

Citation Number: 148

Abstract

Four new synthetic routes to meso-tetraarylporphyrins using a MacDonald-type 2+ 2 condensation are described. Self-condensation of a 5-'aryldipyrromethane (eg, 17) with an aryl-substituted onecarbon bridging unit affords a mixture of tetraarylporphyrins due to acid- catalyzed redistribution reactions. The second and third methods presented here show wide applicability for the preparation of 5, 10, 15, 20-tetraaryl-substituted porphyrins (eg, 31, 37, ...