Part 2 of Transamidation Reactions (part of the dissertation of U. Kramer). This work was supported by the Schweizerischer Nationalfonds zur Förderung der wissenschaftlichen Forschung.—Part 1: .
The “Zip” Reaction: A New Method for Ring Expansion; Synthesis of 17- and 21- Membered Polyaminolactams†
Article first published online: 22 DEC 2003
Copyright © 1977 by Verlag Chemie, GmbH, Germany
Angewandte Chemie International Edition in English
Volume 16, Issue 12, pages 861–862, December 1977
How to Cite
Kramer, U., Guggisberg, A., Hesse, M. and Schmid, H. (1977), The “Zip” Reaction: A New Method for Ring Expansion; Synthesis of 17- and 21- Membered Polyaminolactams. Angew. Chem. Int. Ed. Engl., 16: 861–862. doi: 10.1002/anie.197708611
- Issue published online: 22 DEC 2003
- Article first published online: 22 DEC 2003
- Manuscript Received: 22 SEP 1977
Large nitrogen-containing rings are preparable in very good yields by the “zip” reaction. Thus the 17-membered lactam can be transformed, as the Na salt, into (2) by reaction with acrylonitrile and then with H2/Pt; in the presence of K[NH(CH2)3NH2], (2) rearranges with ring expansion to (3). Compound (1) was obtained analogously from the 13-membered lactam.