Photochemical reaction of 7-aminocoumarins. 9. [2+2]-Cycloadducts with trans,trans-1,4-diphenyl-1,3-butadiene

The photoreactions of 7-diethylaminocoumarin, 4-methyl-7-diethylaminocoumarin, 4-trifluoromethyl-7-diethylaminocoumarin, and 4-N-morpholino-7-diethylaminocoumarin with trans,trans-1,4-diphenyl-1,3-butadiene, which lead to the formation of [2+2]-cycloaddition products, were studied. It was established that photocycloaddition proceeds with the formation of adducts that have a 1-endo-styryl substituent and a 2-exo-phenyl group. The effect of the substituent in the 4-position of the 7-aminocoumarin molecule on the effectiveness of cycloaddition is discussed.See [1] for Communication 8.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1319–1325, October, 1990.