Cycloreversion of 1,5-Diarylcyclobutene in a Photosensitized Reaction

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9,1O-Dicyanoanthracene (DCA)-sensitized cycloreversion of 1,5-diphenylbicyclo-[3.2.0]hept-6-ene (1a) and 5-(1-naphthy1)-4-phenyl bicyclo[3.2.0] hept-6-ene (1b) to 1,4-diphenylcyclohepta- 1,3-diene (2a) and 1-(1-naphthyl)-4-phenylcyclohepta-1,3-diene (2b), respectively, occurred with high quantum yield in acetonitrile or benzene at room temperature. The mechanism is discussed in terms of electron transfer from 1 to the excited singlet state of DCA. The cycloreversion of radical cation of 1 (1+) occurred rapidly even at 77K in pulse radiolysis and γ -radiolysis. It is suggested that cycloreversion of 1+ occurs in the mechanism involving cleavage of Cl-C5 σ -bond and cyclic reaction of Cl-C5 σ-orbitals and C6-C7 π-orbitals.

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