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Intramolecular [4+2]-cycloaddition reactions of cyclic 2-thiomethyl-5-amidofurans

โœ Scribed by John D Ginn; Stephen M Lynch; Albert Padwa

Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
85 KB
Volume
41
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

Cyclic 2-thiomethyl-5-amidofurans possessing tethered p-bonds were prepared by a dimethyl(methylthio) sulfonium tetrafluoroborate (DMTSF) induced cyclization of various amido dithioacetals. Upon heating, these systems undergo an intramolecular 4+2-cycloaddition reaction. The initially formed Diels-Alder cycloadduct further rearranges by ring opening of the oxygen bridge followed by a subsequent 1,2-thiomethyl shift.

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