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Communication | Special issue | Vol 28, No. 2, 1989, pp.633-638
Published online, 1st January, 1970
DOI: 10.3987/COM-88-S93
4,9-Methano-1H-aza[11]annulene: A 12π-Homologue of Pyrrole

Walter Lange, Wilhelm Haas, Hans Schmickler, and Emanuel Vogel*

*Institut für Organische Chemie, Universität zu Köln, Greinstraße 4, D-50939 Köln 41, Germany

Abstract

4,9-Methano-1H-aza[11]annulene (3), to be regarded as a 12π-homologue of pyrrole, was synthesized from 1,6-methano[10]annulene by a reaction sequence patterned after that employed in the conversion of benzene to 1H-azepine (1). In contrast to 1, which is atropic, 3 - a bridged structural variant of the elusive 1H-aza[11]annulene - qualifies as paratropic, although its peripheral elevenmembered ring possesses a non-planar conformation.