9,12-Difluoro-and 9,12-dichlorotetracyclo[188.8.131.52.12.02.7] hexadeca-2,4,6,13,15-pentaene-10,11 -dicarboxylic anhydrides (2a) and (2b) were prepared by 4πs + 4πs is photocycloaddition between cis-3,6-difluoro-or cis-3,6-dichloro-1,2-dihydrophthalic anhydride and naphthalene, respectively. 12, 15-Difluoro-and 12, 15-dichlorohexacyclo [8.6.0.02.15.03.8.09.12.011.16] hexadeca-3,5,7-triene-13,14-dicar-boxylic anhydrides (6a) and (6b) were obtained by 2πs + 2πs is intramolecular photocycloaddition of adducts (2a) and (2b), respectively. 12,15-Difluorohexacyclo[8.6.0.02.15.03.8.09.12.011.16]hexadeca-3,5,7,13-tetraene (7a) has been synthesized by the electro-oxidative decarboxylation of anhydride (6a) and the excited singlet naphthalene has been observed on irradiation of adduct (7a), and is presumably formed via an adiabatic pathway.
|Number of pages||4|
|Journal||Journal of the Chemical Society, Perkin Transactions 1|
|Publication status||Published - Jan 1 1988|
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