Preparation of Azulene-Derived Fulvenedialdehydes and Their Application to the Synthesis of Stable adj-Dicarbaporphyrinoids

…, AD Lammer, AS Idate, DA Colby…

Index: Lash, Timothy D.; Lammer, Aaron D.; Idate, Aparna S.; Colby, Denise A.; White, Kristen Journal of Organic Chemistry, 2012 , vol. 77, # 5 p. 2368 - 2381

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Citation Number: 21

Abstract

A “2+ 2” strategy for synthesizing adj-dicarbaporphyrinoid systems has been developed. In a model study, an azulenylmethylpyrrole dialdehyde was condensed with a dipyrrylmethane in the presence of HCl, followed by oxidation with ferric chloride, to give a modest yield of an azuliporphyrin. Fulvene aldehydes were prepared by reacting an indene-derived enamine with azulene aldehydes in the presence of Bu2BOTf, and azulene dialdehydes similarly ...