Photocyclization of. alpha.-keto amides in homogeneous solution and aqueous cyclodextrin media. The role of zwitterions and diradicals in photoinduced electron …

CA Chesta, DG Whitten

Index: Chesta, Carlos A.; Whitten, David G. Journal of the American Chemical Society, 1992 , vol. 114, # 6 p. 2188 - 2197

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Citation Number: 29

Abstract

Abstract: A mechanistic investigation of the photoreaction of the N, N-disubstituted benzoyl amides, PhCOCONR'R” 1-4 (1: R'= C2HS, R”= Ph; 2: R'= R”= C2H5; 3: R'= R”= CH2Ph; 4: R'= R”= i-C3H7), in homogeneous solutions (water, methanol) and aqueous cyclodextrin is reported. The chief photoproducts, oxazolidin-4-ones, 3-hydroxyazetidin-2-ones, mandelamides, and carbonyl compounds, can all be accounted for by a mechanism ...