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

Authors
Ginn, JD Lynch, SM Padwa, A
Citation
Jd. Ginn et al., Intramolecular [4+2]-cycloaddition reactions of cyclic 2-thiomethyl-5-amidofurans, TETRAHEDR L, 41(49), 2000, pp. 9387-9391
Citations number
19
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
49
Year of publication
2000
Pages
9387 - 9391
Database
ISI
SICI code
0040-4039(200012)41:49<9387:I[ROC2>2.0.ZU;2-2
Abstract
Cyclic 2-thiomethyl-5-amidofurans possessing tethered pi -bonds were prepar ed by a dimethyl(methylthio) sulfonium tetrafluoroborate (DMTSF) induced cy clization of various amido dithioacetals. Upon heating, these systems under go 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. (C) 2000 Elsevier Science Lt d. All rights reserved.