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Photoinduced [2 + 2] cycloaddition (the Paterno–Büchi reaction) of N-methyl-4,5,6,7-tetrachlorophthalimide with alkenes

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Photoinduced reactions of N-methyl-4,5,6,7-tetrachlorophthalimide (TCP) with styrene (1a), p-methylstyrene (1b), α-methylstyrene (1c) and indene (1d) in benzene follow the Paterno–Büchi reaction pathway to give the corresponding diastereoisomeric spirooxetanes as main products. This is in contrast with the photoreactions of N-methylphthalimide (NMP) with alkenes, which furnish the benzazepinediones as main products. In the case of 1d, addition products derived from single electron transfer (SET) between TCP* and the alkene followed by proton transfer in the (TCP–·1d) ion radical pair and subsequent (TCP ketyl–indene's allylic) radical pair recombination were also formed. Photoreactions of TCP with 1a and 1c in methanol-chloroform, on the other hand, are dominated by SET process and gave the solvent incorporated addition products.


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