REARRANGEMENT AND CYCLIZATION OF BETA-MESYLOXY KETONES - SYNTHESIS OFDELTA-SULTONES

Authors
DEKIMPE N BOEYKENS M LAZAR L SZAKONYI Z KEMME A DUBURS G
Citation
N. Dekimpe et al., REARRANGEMENT AND CYCLIZATION OF BETA-MESYLOXY KETONES - SYNTHESIS OFDELTA-SULTONES, Bulletin des Societes chimiques belges, 103(5-6), 1994, pp. 299-302
Citations number
18
Categorie Soggetti
Chemistry
Journal title
Bulletin des Societes chimiques belges → ACNP
ISSN journal
00379646
Volume
103
Issue
5-6
Year of publication
1994
Pages
299 - 302
Database
ISI
SICI code
0037-9646(1994)103:5-6<299:RACOBK>2.0.ZU;2-U
Abstract
The reactivity of beta-mesyloxy ketones towards N-nucleophiles and bas es was evaluated. In the presence of titanium(IV) chloride, the reacti on with primary amines leads to the formation of beta-mesyloxy imines and beta-amino imines. Upon base treatment, beta-mesyloxy ketones unde rwent cyclization to delta-sultones. Increasing steric hindrance in be ta-mesyloxy ketones changed the reaction course and gave rise to the f ormation of cyclobutanones and 2-methyleneoxetanes.