REVERSE-COPE-CYCLIZATIONS OF THIAHYDROXYLAMINES DERIVED FROM THE ADDITION OF ALLYLIC THIOLS TO NITRONES - SYNTHESES OF 1,3-THIAZOLIDINE-N-OXIDES AND 1,5,2-OXATHIAZINANES

Authors
COOGAN MP GRAVESTOCK MB KNIGHT DW THORNTON SR
Citation
Mp. Coogan et al., REVERSE-COPE-CYCLIZATIONS OF THIAHYDROXYLAMINES DERIVED FROM THE ADDITION OF ALLYLIC THIOLS TO NITRONES - SYNTHESES OF 1,3-THIAZOLIDINE-N-OXIDES AND 1,5,2-OXATHIAZINANES, Tetrahedron letters, 38(49), 1997, pp. 8549-8552
Citations number
16
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
49
Year of publication
1997
Pages
8549 - 8552
Database
ISI
SICI code
0040-4039(1997)38:49<8549:ROTDFT>2.0.ZU;2-B
Abstract
Allylthiols 7 react as nucleophiles with nitrones 8 to give intermedia te thiahydroxylamines which undergo reverse-Cope cyclisations to provi de 1,3-thiazolidine-N-oxides 9; in the case of derivatives of C-phenyl nitrone, thermolysis results in smooth Meisenheimer rearrangement lea ding to the 1,5,2-oxathiazinane 14. (C) 1997 Elsevier Science Ltd.