Abstract
Efficient cross-photoaddition of 3-( trans-1-propenyl)coumarin ( 1a) to olefins occurred to give the corresponding 4- and/or 5-substituted 3-( trans-1-propenyl)-3,6-dihydrocyclobut[ c]-2-coumarin in relatively good yields without the formation of dimer of 1a. The photoaddition of 3-ethenylcoumarin ( 1b) and 2-ethenyl-8-methoxycoumarin ( 1c) to 2,3-dimethyl-2-butene ( 2a) gave the corresponding cycloadducts along with the formation of the photodimers of 1b or 1c. Kinetic data show that the photoaddition of 1a to 2a in benzene proceeds via a singlet exciplex between 1a and 2a and the photoaddition in acetonitrile proceeds via a termolecular interaction of a polar exciplex with another 2a.
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