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Paper | Special issue | Vol 40, No. 2, 1995, pp.639-652
Published online, 1st January, 1970
DOI: 10.3987/COM-94-S51
Azobridges from Azines XIII. Azobridged Polycycles: Skeletal Reaarangements by Denitrogenation of Triazolines and Solvolyses of Aziridines

Siegfried Hünig and Petra Kraft

*Institüte of Organic Chemistry, University of Würzburg, Am Hubland, D-97074 Würzburg, Germany

Abstract

Triazolines (2, 6 and 12) derived from the corresponding azobridged polycycles undergo rapid denitrogenation in the presence of several heterogeneous acids (e.g. silica gel) with formation of the aziridines (3, 7, and 13) together with the rearrangement products (4) and (8). In addition to 7 and 8, further products are formed on extrusion of nitrogen from 6 by dissolved acids, especially formic acid. In these reactions the azo group of 6 is involved, and hydrazine (9) and enamine (10) are produced. These two products are also isolated from the very slow acid catalyzed rearrangement of aziridine (7). The most likely reaction paths are exemplified with triazoline (6) in Scheme 1.