Exploratory and Mechanistic Studies of the Electron-Transfer-Initiated Photoaddition Reactions of Allylsilane-Iminium Salt Systems

Article abstract of DOI:10.1021/jo00176a001

Exploratory studies have uncovered novel photoaddition reactions occuring upon irradiation of 1-methyl-2-phenyl-1-pyrrolinium perchlorate (4) in the presence of a variety of allylsilanes 5-10 and leading to production of 2-allylpyrrolidine photoadducts.Mechanistic studies demonstrate that the reactions occur from the singlet excited state of 4.The effects of substituents on the allylsilane component on the reaction quantum efficiencies have been probed.Mechanisms for these processes involving electron transfer and cation radical desilylation are discussed.