A new intramolecular migration in thiosugar chemistry: S -> O transfer of a benzothiazol-2-yl group in saccharidic sulfones

Authors
Gueyrard, D Lorin, C Moravcova, J Rollin, P
Citation
D. Gueyrard et al., A new intramolecular migration in thiosugar chemistry: S -> O transfer of a benzothiazol-2-yl group in saccharidic sulfones, J CARB CHEM, 18(3), 1999, pp. 317-331
Citations number
13
Categorie Soggetti
Chemistry & Analysis
Journal title
JOURNAL OF CARBOHYDRATE CHEMISTRY
ISSN journal
07328303 → ACNP
Volume
18
Issue
3
Year of publication
1999
Pages
317 - 331
Database
ISI
SICI code
0732-8303(1999)18:3<317:ANIMIT>2.0.ZU;2-G
Abstract
Saccharidic benzothiazol-2yl sulfones - readily obtained through regioselec tive Mitsunobu thiofunctionalization followed by standard S-oxidation - can easily undergo benzothiazol-2-yl group S --> O transfer when submitted to the action of a hindered base under controlled conditions. An ipso-substitu tion process is the key-step of this novel intramolecular rearrangement of saccharidic sulfones.