Reaction of vinylcarbenoids with thioketones: formation of vinylthiocarbonyl ylides followed by ring closure to thiiranes and dihydrothiophenes

Authors
Hamaguchi, M Funakoshi, N Oshima, T
Citation
M. Hamaguchi et al., Reaction of vinylcarbenoids with thioketones: formation of vinylthiocarbonyl ylides followed by ring closure to thiiranes and dihydrothiophenes, TETRAHEDR L, 40(46), 1999, pp. 8117-8120
Citations number
25
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
46
Year of publication
1999
Pages
8117 - 8120
Database
ISI
SICI code
0040-4039(19991112)40:46<8117:ROVWTF>2.0.ZU;2-T
Abstract
Reactions were carried out on thioketones with vinylcarbenoids. Rh-2(OAc)(4 )-catalyzed reaction of vinyldiazo compounds 1a,b with xanthione 2 and thio chromone 3 gave thiiranes 4b and olefins 5 and 6, desulfurization products from thiiranes, while the reaction of 1c with 2 and 3 afforded dihydrothiop henes 7, 8 and 9. (C) 1999 Elsevier Science Ltd. All rights reserved.