Based on a lecture given in Regensburg on July 3, 1972.
Article first published online: 22 DEC 2003
Copyright © 1973 by Verlag Chemie, GmbH, Germany
Angewandte Chemie International Edition in English
Volume 12, Issue 6, pages 464–473, June 1973
How to Cite
Köbrich, G. (1973), Bredt Compounds and the Bredt Rule. Angew. Chem. Int. Ed. Engl., 12: 464–473. doi: 10.1002/anie.197304641
Dedicated to Professor Theodor Wieland on the occasion of his 60th birthday
- Issue published online: 22 DEC 2003
- Article first published online: 22 DEC 2003
- Manuscript Received: 22 SEP 1972
- Bredt rule;
- Bridgehead alkenes;
- Bicyclic systems
The Bredt rule, which proved useful in earlier decades mainly as an exclusion criterion in the assignment of structures, has in recent years become the stimulus for efforts to synthesize strained bicyclic systems with a bridgehead double bond. On the basis of the ring-strain forces operating in such systems, an extended Bredt rule is discussed. The “Bredt comgounds” to which this rule applies, which include bicyclic systems not prevoously consodered from this point of view (e.g. bridged methylenecyclopropanes), form a clearly circumscribed, interesting field within the chemistry of highly-strained hydrocarbons with ring unsaturation.