Title of article
Intramolecular [4+2]-cycloaddition reactions of cyclic 2-thiomethyl-5-amidofurans
Author/Authors
Ginn، نويسنده , , John Peder and Lynch، نويسنده , , Stephen M and Padwa، نويسنده , , Albert، نويسنده ,
Issue Information
هفته نامه با شماره پیاپی سال 2000
Pages
5
From page
9387
To page
9391
Abstract
Cyclic 2-thiomethyl-5-amidofurans possessing tethered π-bonds were prepared by a dimethyl(methyl-thio) 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.
Keywords
cyclization , amidofuran , Diels–Alder , Intramolecular , DMTSF , Pummerer
Journal title
Tetrahedron Letters
Serial Year
2000
Journal title
Tetrahedron Letters
Record number
1640226
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