NEIGHBORING GROUP PARTICIPATION IN PUMMERER-TYPE REARRANGEMENTS OF ORTHO-SUBSTITUTED ARYLMETHYL SULFOXIDES

Authors
FINDLAY JBC FISHWICK CWG KERSEY ID WARD P
Citation
Jbc. Findlay et al., NEIGHBORING GROUP PARTICIPATION IN PUMMERER-TYPE REARRANGEMENTS OF ORTHO-SUBSTITUTED ARYLMETHYL SULFOXIDES, Tetrahedron letters, 36(13), 1995, pp. 2299-2302
Citations number
13
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
36
Issue
13
Year of publication
1995
Pages
2299 - 2302
Database
ISI
SICI code
0040-4039(1995)36:13<2299:NGPIPR>2.0.ZU;2-M
Abstract
The presence of an ortho hydroxymethyl group in arylmethyl sulphoxides results in the exclusive formation of chloromethyl sulphides, mediate d via an intramolecular attack to yield an alkoxysulphonium salt. This intramolecular attack prevents the formation of siloxymethyl sulphide s which would result via the sila-Pummerer rearrangement.