Abstract
Photosensitized cycloreversion of the photodimer of methyl 2-naphthoate ( 1) by using 1-cyanonaphthalene (CN), 9,10-dicyanoanthracene (DCA) and chloranil (CHL) as sensitizers has been examined. 1 can efficiently isomerize to its monomer, methyl 2-naphthoate ( 2), by a reversible electron transfer or exciplex mechanism. In the case of using singlet sensitizers (CN and DCA), the cycloreversion of 1 to 2 proceeded via an efficient cation-radical chain process in acetonitrile, while in dichloromethane and benzene 1 isomerized to 2 through an exciplex or partial charge transfer. For triplet sensitizer CHL, in all solvents examined the reaction occurred through a cation-radical chain process, and the efficiencies were higher compared with those for the singlet sensitizers. This cycloreversion likely involves two [2+2] processes.
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