CONVERSION OF A DIARYLSULFOXIDE TO CYCLIC SULFONIUM YLIDE - DEHYDRATION WITH SIGMA-BOND SHIFT AND DECARBOXYLATION

Authors
KUTI M RABAI J KAPOVITS I KUCSMAN A PARKANYI L ARGAY G KALMAN A
Citation
M. Kuti et al., CONVERSION OF A DIARYLSULFOXIDE TO CYCLIC SULFONIUM YLIDE - DEHYDRATION WITH SIGMA-BOND SHIFT AND DECARBOXYLATION, ACH, models in chemistry, 131(3-4), 1994, pp. 313-325
Citations number
24
Categorie Soggetti
Chemistry
Journal title
ACH, models in chemistry → ACNP
ISSN journal
12178969
Volume
131
Issue
3-4
Year of publication
1994
Pages
313 - 325
Database
ISI
SICI code
1217-8969(1994)131:3-4<313:COADTC>2.0.ZU;2-F
Abstract
2-(2-Acetylaminophenylsulfinyl)benzoic acid (4) has been converted to acyl-stabilized cyclic sulfonium-ylide (5) by heating with trifluoroac etic anhydride in DMF. The structure of the product has been determine d by X-ray diffraction. The sulfurane-like configuration and the solid -state conformation revealing sulfur-oxygen close contacts are discuss ed. A mechanism is proposed for the dehydration reaction involving sig ma-bond shift and decarboxylation.