Use of 2,3-dibromo-1-(phenylsulfonyl)-1-propene as a reagent for the synthesis of annulated furans

Treatment of 2,3-dibromo-1-(phenyl-sulfonyl)-1-propene with various .beta.-dicarbonyl compounds in the presence of sodium methoxide affords 2,4-disubstituted and 2,3-fused bicyclic furans in high yield. Formation of the furan ring involves a sequence of addition-elimination, deacetylation, and SN2 d...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 55; no. 14; pp. 4241 - 4242
Main Authors Padwa, Albert, Murphree, S. Shaun, Yeske, Philip E
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 01.07.1990
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Organic chemistry
Physical Sciences
Preparations and properties
Science & Technology
Cycloaddition
Base catalysis
Sulfone
Bicyclic compound
Bromine Organic compounds
Diketone
Oxygen heterocycle
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ISSN0022-3263
1520-6904
DOI10.1021/jo00301a006

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Summary:Treatment of 2,3-dibromo-1-(phenyl-sulfonyl)-1-propene with various .beta.-dicarbonyl compounds in the presence of sodium methoxide affords 2,4-disubstituted and 2,3-fused bicyclic furans in high yield. Formation of the furan ring involves a sequence of addition-elimination, deacetylation, and SN2 displacement reactions.
Bibliography:ark:/67375/TPS-HMZ6807X-S
istex:990D83A026FAACBEC363B67E6F1F119C2AEF2A12
ISSN:0022-3263
1520-6904
DOI:10.1021/jo00301a006