TANDEM PUMMERER DIELS-ALDER SEQUENCE FOR THE PREPARATION OF ALPHA-THIO SUBSTITUTED NAPHTHALENE DERIVATIVES

Authors
COCHRAN JE PADWA A
Citation
Je. Cochran et A. Padwa, TANDEM PUMMERER DIELS-ALDER SEQUENCE FOR THE PREPARATION OF ALPHA-THIO SUBSTITUTED NAPHTHALENE DERIVATIVES, Tetrahedron letters, 36(20), 1995, pp. 3495-3498
Citations number
17
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
36
Issue
20
Year of publication
1995
Pages
3495 - 3498
Database
ISI
SICI code
0040-4039(1995)36:20<3495:TPDSFT>2.0.ZU;2-J
Abstract
The alpha-thiocarbocation generated from the Pummerer reaction of an o -benzoyl substituted sulfoxide is intercepted by the adjacent keto gro up to produce an alpha-thio-isobenzofuran as a transient intermediate which undergoes a subsequent Diels-Alder cycloaddition with added dien ophiles.