Unusually facile dealkylation of alkyl 2-(methylthiomethyl)phenyl sulfoxides with triflic anhydride via dithia dications: Stereochemical and kinetic studies

Authors
Naka, H Maruyama, T Sato, S Furukawa, N
Citation
H. Naka et al., Unusually facile dealkylation of alkyl 2-(methylthiomethyl)phenyl sulfoxides with triflic anhydride via dithia dications: Stereochemical and kinetic studies, TETRAHEDR L, 40(2), 1999, pp. 345-348
Citations number
9
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
2
Year of publication
1999
Pages
345 - 348
Database
ISI
SICI code
0040-4039(19990108)40:2<345:UFDOA2>2.0.ZU;2-Q
Abstract
Alkyl 2-(methylthiomethyl)phenyl sulfoxides undergo facile monodealkylation on treatment with triflic anhydride in CH3CN to afford the corresponding t hiasulfonium salts and alkyl iminium salts quantitatively. The dealkylation proceeds by an S(N)1 process which gives thiasulfonium salt and alkyl cati on via an initial formation of the corresponding dithia dication species. ( C) 1998 Elsevier Science Ltd. All rights reserved.