ORGN 459 |
| Irradiation of degassed solution of 3-azide-3-phenyl propiophenone 1 via Pyrex filter produced primarily phenyl[3-phenyl-2-aziridinyl]methanone 2. The formation of 2 can be described as the cleavage of azide radical which abstracts H-atom from the solvent to form hydrazoic acid. Further photolysis of the hydrazoic acid yields singlet imidogen that inserts into radical 3 to give azridine product. This is further confirmed by doing photolysis in the presence of tris(trimethylsily)silane, which resulted in 3-phenyl propiophenone 4 showing the cleavage of C-N3 bond. Photolysis of 4'-methoxy-3-azide-3-phenyl propiophenone and 4'-chloro-3-azide-3-phenyl propiophenone also resulted in aziridinyl formation, demonstrating that this reaction can be used as a general method for synthesis of aziridinyl derivatives.
|
|
New Reactions, Methodology, Total Synthesis, Physical Organic Chemistry
8:00 PM-10:00 PM, Tuesday, 15 March 2005 Convention Center -- Sails Pavilion, Poster
Division of Organic Chemistry |
