Synthesis, Spectroscopy, and Reactivity of m eso-Unsubstituted Azuliporphyrins and Their Heteroanalogues. Oxidative Ring Contractions to Carba-, Oxacarba-, …

…, DA Colby, SR Graham, ST Chaney

Index: Lash, Timothy D.; Colby, Denise A.; Graham, Shelley R.; Chaney, Sun T. Journal of Organic Chemistry, 2004 , vol. 69, # 25 p. 8851 - 8864

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Citation Number: 66

Abstract

This paper reports the first detailed study on meso-unsubstituted azuliporphyrins, an important family of porphyrin-like molecules where one of the usual pyrrole rings has been replaced by an azulene subunit. Although the azulene moiety introduces an element of cross-conjugation, zwitterionic resonance contributors with tropylium and carbaporphyrin substructures give azuliporphyrins diatropic character that falls midway between true ...