671777-78-9Relevant articles and documents
β-Lactam-Forming Photochemical Reactions of N-Trimethylsilylmethyl- and N-Tributylstannylmethyl-Substituted α-Ketoamides
Wang, Runtang,Chen, Chuanfeng,Duesler, Eileen,Mariano, Patrick S.,Yoon, Ung Chan
, p. 1215 - 1220 (2004)
Two mechanisms have been proposed for the β-lactam-forming photochemical reactions of α-ketoamides. One, suggested by Aoyama, involves excited-state H-atom abstraction while the other, put forth by Whitten, follows a sequential SET-proton-transfer route. The photochemical properties of N-trimethylsilylmethyl- and N-tributylstannylmethyl-substituted α-ketoamides were explored in order to gain information about the mechanism of this process and to develop a regioselective method for β-lactam formation. The results of this effort show that (1) photoreactions of N-trimethyl-silylmethyl-substituted α-ketoamides proceed by competitive H-atom abstraction and sequential SET-desilylation pathways and (2) a sequential SET-destannylation pathway is preferentially followed in photochemical reactions of the tributylstannylmethyl-substituted α-ketoamides.