Mechanism of cheletropic reactions of 1,3-dienes with sulfur dioxide
Article first published online: 4 DEC 1998
Copyright © 1996 John Wiley & Sons, Ltd.
Journal of Physical Organic Chemistry
Volume 9, Issue 1, pages 17–20, January 1996
How to Cite
Suárez, D., Iglesias, E., Sordo, T. L. and Sordo, J. A. (1996), Mechanism of cheletropic reactions of 1,3-dienes with sulfur dioxide. J. Phys. Org. Chem., 9: 17–20. doi: 10.1002/(SICI)1099-1395(199601)9:1<17::AID-POC749>3.0.CO;2-D
- Issue published online: 4 DEC 1998
- Article first published online: 4 DEC 1998
- Manuscript Accepted: 11 SEP 1995
- Manuscript Received: 10 JUL 1995
In a recent paper [N.S. Isaacs and A. Laila, J. Phys. Org. Chem. 7, 178 (1994)2] the volume profile for the cheletropic addition of sulphur dioxide to a 1,3-diene (2,3-dimethylbuta-1,3-diene) indicated that a two-step mechanism for this reaction, with a (4 + 2) cycloaddition at the S(DOUBLE BOND)O bond as the slow step followed by a rapid rearrangement of the resultant sulpheno-lactone, cannot be ruled out. However, ab initio calculations, at the MP2(FC)/6-31G*//RHF/6-31G* level, show that such a mechanism can be conclusively discarded.