Add time:09/25/2019 Source:sciencedirect.com
[3+2]-Photocycloadditions of 1,2-, 1,3-, and 2,3-dicyanonaphthalenes to alkenes were found to proceed at the 1,8-, 4,5-, and 1,8-positions of the naphthalene ring of dicyanonaphthalenes, respectively. In the photoreactions of the 1,3- and 2,3-isomers [3+2]-adducts were obtained in oxidized forms and addition of Cu(OAc)2 considerably improved the yields of the adducts. The observed addition sites of the alkenes are rationalized on the basis of the spin and charge densities of the radical anions of dicyanonaphthalenes.
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