Photolysis of α-Azidoacetophenones:  Trapping of Triplet Alkyl Nitrenes in Solution

Autor: Mandel, S. M., Bauer, J. A. Krause, Gudmundsdottir, A. D.
Zdroj: Organic Letters; February 2001, Vol. 3 Issue: 4 p523-526, 4p
Abstrakt: Selective excitation of the ketone chromophore in α-azidoacetophenones, 1, leads to intramolecular triplet energy transfer to the azido group, which forms the corresponding triplet alkyl nitrene, 2. Azides 1 also undergo α-cleavage to form benzoyl and methyl azido radicals in competition with nitrene formation. Thus the major photoproduct, 2-benzoylamino-1-phenylethanone, 3, comes from trapping of 2 with a benzoyl radical. This appears to be the first observation of bimolecular trapping of triplet alkyl nitrenes in solution.
Databáze: Supplemental Index