Intermolecularly hydrogen-bonded dimeric helices: tripyrrindiones

SD Roth, T Shkindel, DA Lightner

Index: Roth, Steven D.; Shkindel, Tetyana; Lightner, David A. Tetrahedron, 2007 , vol. 63, # 45 p. 11030 - 11039

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Citation Number: 12

Abstract

A rare and unusual class of tripyrrolic compounds, violet-colored tripyrrin-1, 14-diones, can be prepared easily and in moderately high yields from base (piperidine)-catalyzed condensation of 3-pyrrolin-2-ones with 2, 5-diformylpyrroles. Dipyrrinones adopt the all-syn- Z conformation leading to helical, lock-washer like structures, which form dimers that are held together by intermolecular hydrogen bonds in nonpolar solvents and in the crystal. ...