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Synthesis 2004(14): 2297-2302
DOI: 10.1055/s-2004-831201
DOI: 10.1055/s-2004-831201
PAPER
© Georg Thieme Verlag Stuttgart · New York
Synthesis of Fluoroalkyl Vinyl Sulfoxides and their Use in Diels-Alder Reactions
Further Information
Received
19 May 2004
Publication Date:
25 August 2004 (online)
Publication History
Publication Date:
25 August 2004 (online)
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Abstract
Condensation of various dienes with fluoroalkyl vinyl sulfoxides was studied. Four diastereoisomers were obtained in the case of cyclopentadiene and their structures were assigned by 2D NMR experiments. Diels-Alder cycloaddition occurred with cyclohexadiene, in comparison to phenyl vinyl sulfoxide, without thermal extrusion of fluoroalkylsulfenic acid. Condensation with anthracene led to a mixture of compounds 11 and 12.
Key words
acetylene equivalent - Diels-Alder reactions - eliminations - fluorine - sulfoxides
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References
The literature indicates that the cycloaddition of Danishefsky’s diene with phenyl vinyl sulfoxide required temperatures of ca. 135-150 °C without description of the products formed.