8H-ANHYDRO-4-HYDROXY-2-OXO-1,3-THIAZINIUM HYDROXIDES AS MESOIONIC 1,4-DIPOLES

Authors
PADWA A COATS SJ HADJIARAPOGLOU L
Citation
A. Padwa et al., 8H-ANHYDRO-4-HYDROXY-2-OXO-1,3-THIAZINIUM HYDROXIDES AS MESOIONIC 1,4-DIPOLES, Heterocycles, 39(1), 1994, pp. 219-241
Citations number
75
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Heterocycles → ACNP
ISSN journal
03855414
Volume
39
Issue
1
Year of publication
1994
Pages
219 - 241
Database
ISI
SICI code
0385-5414(1994)39:1<219:8HAM1>2.0.ZU;2-F
Abstract
The previously unknown 8H-anhydro-4-hydroxy-2-oxo-1,3-thiazinium hydro xides (1) were prepared and their 1,4-dipolar cycloaddition behavior w as examined. In most cases, elimination of the proton in the 8-positio n of the mesoionic ring was observed to occur unless extremely reactiv e dipolarophiles were used. The S,N-ketene acetals were converted to t he corresponding alpha-diazo ketones for further study.