ISSN:
0941-1216
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Reactions of 2-phenyl (1a) and 2-benzyl (1b) 1-benzoyl-2-butylaziridines with carbanions X-, AH-, and Fl- of xanthene, dihydroanthracene and fluorene always form N-(2-butylethyl)-benzamides carrying phenyl (9a) or benzyl (9b). This reductive ring opening indicates an SET mechanism with aziridino ketyls 6a, b as intermediates. Nucleophilic ring opening (SNs) is found only with the carbanion of the lowest reducing power: Fl- → 5a, b (62%, 14%). These two mechanisms cleave different bonds, a finding without precedence in SN2/SET competitions. Carbonyl addition resulting in benzoyl transfer to xanthene, dihydroanthracene or fluorene is usually also observed. It is the main reaction with X- and 1a. The highest yields of 9a, b are obtained with AH- since a special inner-sphere SET is available.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/prac.19953370157
Permalink