Additions of nucleophiles to 3-oxo-2,3-dihydrothiophene 1,1-dioxides. Formation of vinyl sulfides, thioacetals and enaminones

Citation
Nu. Hofslokken et L. Skattebol, Additions of nucleophiles to 3-oxo-2,3-dihydrothiophene 1,1-dioxides. Formation of vinyl sulfides, thioacetals and enaminones, J CHEM S P1, (21), 1999, pp. 3085-3088
Citations number
27
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
ISSN journal
0300922X → ACNP
Issue
21
Year of publication
1999
Pages
3085 - 3088
Database
ISI
SICI code
0300-922X(19991107):21<3085:AONT31>2.0.ZU;2-Q
Abstract
3-Oxo-2,3-dihydrothiophene 1,1-dioxide (1a) was prepared by oxidation of th e commercially available 3-methoxythiophene with dimethyldioxirane. Some ot her substituted 3-methoxythiophene derivatives were oxidized as well. Altho ugh the yields of these reactions were low, the one-step method is preferre d to the current literature procedures. 3-Oxo-2,3-dihydrothiophene 1,1-diox ide derivatives reacted with sulfur and nitrogen nucleophiles. Reactions to ok place with extrusion of sulfur dioxide even at room temperature. High yi elds of vinyl sulfides; thioacetals, bis-thioacetals, and enaminones were o btained from these reactions.