Publication
Title
Synthesis of 4,4-disubstituted -lactams by regiospecific electrophile- and silver-induced ring expansion of 2,2-disubstituted 1-methoxycyclopropylamines
Author
Abstract
2,2-Disubstituted 1-methoxycyclopropylamines underwent regiospecific ring expansion to 1,4,4-trisubstituted 2-azetidinones by N-chlorination with tert-butyl hypochlorite and subsequent rearrangement with silver tetrafluoroborate. Upon thermolysis, 4,4-disubstituted beta-lactams suffer a characteristic ring opening to afford beta,gamma-unsaturated carboxylic amides. The reduction of 1,4,4-trisubstituted 2-azetidinones with lithium aluminum hydride afforded 1,2,2-trisubstituted azetidines.
Language
English
Source (journal)
The journal of organic chemistry. - Washington, D.C.
Publication
Washington, D.C. : 1996
ISSN
0022-3263
Volume/pages
61:19(1996), p. 6500-6503
ISI
A1996VJ00600013
Full text (Publishers DOI)
UAntwerpen
Faculty/Department
Publication type
Subject
External links
Web of Science
Record
Identification
Creation 28.01.2013
Last edited 12.04.2017