The photoreactions of phthalimides la-c and a variety of olefins (2a-g) have been investigated. Irradiation of methanol solutions of la in the presence of electron-rich olefins 2a- f leads to formation of methanol-incorporated adducts 3a+ 4a, 9a, b, 19, 29a, b, 30a, b, and 31. Irradiation of acetonitrile solutions of la in the presence of relatively electron-poor aliphatic olefins 2f, g gives ring-enlarged cycloaddition products 23, 32, and 34, probably ...
