Issue 12, 1988

Synthesis and photochemistry of 3,6-difluoro-10,11-benzopentacyclo [6,4,0.0,0.0]dodeca-4,10-diene

Abstract

9,1 2- Difluoro- and 9,12-dichlorotetracyclo[6.4.2.2.0] hexadeca-2,4,6,13,15-pentaene-1 0,1 1-dicarboxylic anhydrides (2a) and (2b) were prepared by 4πs+ 4πs 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[8.6.0.0.0.0.0]hexadeca-3,5,7-triene-13,14-dicarboxylic anhydrides (6a) and (6b) were obtained by 2πs+ 2πs intramolecular photocycloaddition of adducts (2a) and (2b), respectively. 12,15-Difluorohexacyclo[8.6.0.0.0.0.0]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.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1988, 3307-3310

Synthesis and photochemistry of 3,6-difluoro-10,11-benzopentacyclo [6,4,0.0,0.0]dodeca-4,10-diene

M. Kimura, H. Kura, K. Nukada, H. Okamoto, K. Satake and S. Morosawa, J. Chem. Soc., Perkin Trans. 1, 1988, 3307 DOI: 10.1039/P19880003307

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