An efficient route to trans-4,5-dihydrothiophenes and thiazoles via nitrogen and sulfur ylides

Authors
Dawood, KM
Citation
Km. Dawood, An efficient route to trans-4,5-dihydrothiophenes and thiazoles via nitrogen and sulfur ylides, SYN COMMUN, 31(11), 2001, pp. 1647-1658
Citations number
14
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNTHETIC COMMUNICATIONS
ISSN journal
00397911 → ACNP
Volume
31
Issue
11
Year of publication
2001
Pages
1647 - 1658
Database
ISI
SICI code
0039-7911(2001)31:11<1647:AERTTA>2.0.ZU;2-N
Abstract
A number of versatile sulfonium and pyridinium salts reacted stereoselectiv ely with some arylidenecyanothioacetamides under mild heating to give trans -4,5-dihydrothiophenes. The stereochemistry of the products was established on the basis of X-ray analysis. Repeating the same reactions at high tempe rature furnished a mixture of trans-4,5-dihydrothiophenes and thiazoles.