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Photochemical reactions of N-methylphthalimide with silyl enol ethers have been explored. Irradiations of phthalimide (1) and cyclic silyl enol ethers (5a-b) are observed to promote formation of photoreduced phthalimides and photoaddition products by sequential SET-desilylation pathways. The photoreaction of phthalimide (1) and acyclic silyl enol ethers (5c-d) leads to produce oxetanes which arise by competitive single electron transfer (SET) and classical 2+2 photocycloaddition (Parten-Bchi reaction) pathways.