Formation of a new benzotriquinane skeleton via intramolecular photocycloaddition reactions of a phenylethynes moiety to a 1-cyanonaphthalene ring systemDedicated to the memory of Professor Nicholas J. Turro (Columbia University)

Photoirradiation of 1-cyano-2-(2,2-dicyano-5-phenylpentyn-4-yl)naphthalene and its analogues promotes sequential intramolecular [2π + 2π] photocycloaddition and cyclobutene ring opening to form benzocyclooctatetraenes, which are then transformed to benzotriquinanes in good yields via a photochemical...

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Bibliographic Details
Main Authors Mizuno, Kazuhiko, Negoro, Naoki, Nagayama, Yoshinori, Maeda, Hajime, Ikeda, Hiroshi
Format Journal Article
LanguageEnglish
Published 22.01.2014
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Summary:Photoirradiation of 1-cyano-2-(2,2-dicyano-5-phenylpentyn-4-yl)naphthalene and its analogues promotes sequential intramolecular [2π + 2π] photocycloaddition and cyclobutene ring opening to form benzocyclooctatetraenes, which are then transformed to benzotriquinanes in good yields via a photochemical transannular cyclization process. Intramolecular photocycloaddition between cyanonaphthalene and alkynes gave benzotriquinane compounds.
Bibliography:Dedicated to the memory of Professor Nicholas J. Turro (Columbia University).
ISSN:1474-905X
1474-9092
DOI:10.1039/c3pp50243k