Abstract
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–Buchi 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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