The authors thank EPSRC for their support of this programme.
Thermally Induced Cyclobutenone Rearrangements and Domino Reactions†
Article first published online: 5 DEC 2006
Copyright © 2007 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 46, Issue 3, pages 425–428, January 8, 2007
How to Cite
Harrowven, David C., Pascoe, David D. and Guy, Ian L. (2007), Thermally Induced Cyclobutenone Rearrangements and Domino Reactions. Angew. Chem. Int. Ed., 46: 425–428. doi: 10.1002/anie.200603538
- Issue published online: 27 DEC 2006
- Article first published online: 5 DEC 2006
- Manuscript Received: 30 AUG 2006
- domino reactions;
- spiro compounds;
Four thermal-rearrangement pathways and a domino reaction leading to quinones arise from the thermolysis of cyclobutenones. The course of vinylcyclobutenone rearrangements is dictated by the nature of the substituent, R (see scheme): a cyclopentenone arises when R is an electron-rich alkene. In other cases thermolysis gives a cyclohexadienone, which may collapse with elimination to form a quinone, or tautomerize into a hydroquinone or cyclohexenedione.