ISSN:
0941-1216
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The thermal extrusion of SO2 from disubstituted 3-sulfolenes 3 leads to 2,3-donor-acceptor-substituted 1,3-butadienes 4. These dienes react with acrylic acid ester and ethyl vinyl ether to the corresponding Diels-Alder adducts 5 and 6 and with themselves to the cyclic dimerization products 7 and 8. The regiochemistry of the cycloadducts has been determined by chemical- and NMR-methods.The pyrolysis of 3-sulfolene 11 afforded the thiolactone 13 whose structure has been verified by X-ray diffraction analysis. In addition, the influence of Lewis acid catalysts on the Diels-Alder reaction and an approach to transition state calculation by means of the semiempirical AM 1 method has also been investigated.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/prac.19943360413
