Tautomerism in the solid state and in solution of a series of 6-aminofulvene-1-aldimines.

J Org Chem

Departamento de Química Orgánica y Biología, Facultad de Ciencias, UNED, Senda del Rey 9, Eminus sign28040, Madrid, Spain.

Published: March 2002

To study systems able to sustain intramolecular proton-transfer, we have prepared a series of six aminofulvene aldimines including several labeled with (15)N and (2)H. These compounds show coupling constants through the hydrogen bond, (1h)J((15)N- (1)H) and (2h)J((15)N-(15)N). The position of the tautomeric equilibria, i.e., on what nitrogen atom is the proton, was determined in the solid state and in solution. The crystal structure of N[[5-[(phenylamino)methylene]-1,3-cyclopentadien-1-yl]methylene]pyrrole-1-amine (3) has been determined by X-ray analysis. In solution, both N-H and C-H tautomers were observed and their structures assigned by NMR spectroscopy. Particularly useful is the value of the (1)J((15)N-(1)H) coupling constant.

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http://dx.doi.org/10.1021/jo010625vDOI Listing

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