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Investigations in the transition metal catalyzed aziridination of olefins, amination, and other insertion reactions with Bromamine-T as the source of nitrene

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Title Investigations in the transition metal catalyzed aziridination of olefins, amination, and other insertion reactions with Bromamine-T as the source of nitrene
 
Creator Chanda, BM
Vyas, R
Bedekar, AV
 
Subject Chemistry, Organic
 
Description Investigations into the transition metal catalyzed aziridination of olefins with Bromamine-T as a new source of nitrene is presented in this account. Comparison of Chloramine-T and Bromaminel-T in this reaction indicates that the latter is superior as the source of nitrene. Systematic study with several transition metal based catalysts suggests that Cu-halides are the best catalysts. A first report of aziridination under microwave and ultrasound irradiation conditions is also presented. Copper-catalyzed aziridination of methyl cinnamate with Bromamine-T did not proceed at ambient temperature but was effected smoothly under ultrasound irradiation to furnish translaiiridine selectively, while under microwave irradiation, a mixture of cis and trans isomers. was obtained. It has been demonstrated that aziridination of olefins proceeds smoothly with inexpensive bleaching powder. Preliminary results of Rh-catalyzed benzylic insertion reactions with Bromamine-T are included in this account.
 
Publisher AMER CHEMICAL SOCWASHINGTON1155 16TH ST, NW, WASHINGTON, DC 20036 USA
 
Date 2011-09-24T09:30:43Z
2011-09-24T09:30:43Z
2001
 
Type Article
 
Identifier JOURNAL OF ORGANIC CHEMISTRY
0022-3263
http://hdl.handle.net/123456789/24165
 
Language English