Synthesis and photochemistry of 3, 6-difluoro-10,11-benzopentacyclo-[6,4,0.02.7,03.12.06.9]dodeca-4,10-diene

Masaru Kimura, Hisatoshi Kura, Kastumi Nukada, Hideki Okamoto, Kyosuke Satake, Shiro Morosawa

Research output: Contribution to journalArticle

22 Citations (Scopus)

Abstract

9,12-Difluoro-and 9,12-dichlorotetracyclo[6.4.2.29.12.02.7] 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.

Original languageEnglish
Pages (from-to)3307-3310
Number of pages4
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number12
DOIs
Publication statusPublished - Jan 1 1988

ASJC Scopus subject areas

  • Chemistry(all)

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