SYNTHESIS OF SPIROCYCLIC ISOTHIAZOLIUM SA LTS AND THEIR BASE-CATALYZED REACTION TO THIANTHRENES

Authors
SCHULZE B FRIEDRICH B WAGNER S FUHRMANN P
Citation
B. Schulze et al., SYNTHESIS OF SPIROCYCLIC ISOTHIAZOLIUM SA LTS AND THEIR BASE-CATALYZED REACTION TO THIANTHRENES, Journal fur praktische Chemie, Chemiker-Zeitung, 338(5), 1996, pp. 424-429
Citations number
8
Categorie Soggetti
Chemistry,"Chemistry Applied
Journal title
Journal fur praktische Chemie, Chemiker-Zeitung → ACNP
ISSN journal
09411216
Volume
338
Issue
5
Year of publication
1996
Pages
424 - 429
Database
ISI
SICI code
0941-1216(1996)338:5<424:SOSISL>2.0.ZU;2-W
Abstract
N-Phenyl-substituted isothiazolium salts 1 with active 7-methylene gro up react under the influence of bases to the spirocyclic isothiazolium salts raccis- and rac-trans-4; the salts trans-4 are not stable and r eact to the thianthrene derivatives rac-trans-6. Thus, a very simple s eparation of diastereoisomeric salts rac-cis- and rac-trans-4 is possi ble. The influence of donor and acceptor substituents in the phenyl gr oup of 1 on the diastereoselective synthesis of 4 and 6 was studied. T he structure of rac-cis-4 and rac-trans-6 was confirmed by X-ray analy sis.