SELECTIVE TRANSFORMATION OF ALPHA,ALPHA-DIBROMOMETHYL KETONES INTO ALPHA-MONOSULFENYLATED KETONES

Authors
BOEYKENS M DEKIMPE N
Citation
M. Boeykens et N. Dekimpe, SELECTIVE TRANSFORMATION OF ALPHA,ALPHA-DIBROMOMETHYL KETONES INTO ALPHA-MONOSULFENYLATED KETONES, Tetrahedron, 50(43), 1994, pp. 12349-12360
Citations number
24
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
50
Issue
43
Year of publication
1994
Pages
12349 - 12360
Database
ISI
SICI code
0040-4020(1994)50:43<12349:STOAKI>2.0.ZU;2-6
Abstract
When alpha,alpha-dibromomethyl ketones are treated with sodium thiolat es only the alpha-monosulfenylated ketones are formed. Evidence is put forward that the reaction mechanism proceeds by an initial nucleophil ic substitution of one bromo atom and reduction by single electron tra nsfer (SET) - hydrogen atom abstraction of the second bromo atom.