Phthalimide. aminolysis

Photo-addition of alkenes to A methylnaphthalene dicarboxamides in benzene has been studied. The structure of the arene moiety in the imide was important in determining the reaction path. Mainly cyclobutane and oxetan formation occurred. The dicarboximide (342) undergoes photochemical cyclization with incorporation of methanol to yield the two products (343) and (344) in 55 and 16% respectively. This type of cyclization appears to be quite general for such systems and is also reported for the imides (345) and (346). A variety of products resulting from aminolysis, reduction, and radical coupling is produced on irradiation of the phthalimide (347) in diethylamine. ... 

Khan, M.N. Kinetics and mechanism of aminolysis of phthabmide and A-substi-tuted phthalimides evidence for the oeeurrence of intramolecular general acid-base catalysis in the reactions of ionized phthalimides with primary amines. J. Chem. Soc. Perkin Trans. 2. 1990, 435-444. 

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