Synthesis of carboalkoxychloro- and bromodiazirines.
The first known 3H-diazirines bearing a carbonyl group and a halogen atom on C-3 have been prepared by a novel synthetic method. Carboalkoxychloro- and bromodiazirines 1a-d are formed in up to 45% yields by reductive dechlorination of carboalkoxy-N,N,N'-trichloroformamidines 9a,b using chloride or bromide ion. This method constitutes the first example of the use of N,N,N'-trichloroamidines as starting materials in organic synthesis.
Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104, USA. dailey@sas.upenn.edu
Tomas
T
Martinu
William P
WP
Dailey
D003978:Diazomethane / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D006842:Hydrocarbons, Brominated / Q000737:chemistry*; D006843:Hydrocarbons, Chlorinated / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction
D006842:Hydrocarbons, Brominated; D006843:Hydrocarbons, Chlorinated; D003978:Diazomethane