Preparation of polycyclic compounds by intramolecular photospirocyclization and photocycloaddition reactions of 4-alkenyl-1-cyanonaphthalene derivatives

• Published in: Journal of photochemistry and photobiology. A, Chemistry. Vol. 331; pp. 29 - 41
• Main Authors: Maeda, Hajime, Wada, Hidenori, Mukae, Hirofumi, Mizuno, Kazuhiko
• Format: Journal Article
• Language: English
• Published: Lausanne Elsevier B.V 01.12.2016; Elsevier BV
• Subjects: 1-Cyano-4-alkenylnaphthalene; Angular triquinane; Chemical reactions; Photochemistry; Photocycloaddition; Photoreaction; Polycyclic compounds; Spirocyclization; Steric hindrance; 1-Cyano-4-alkenylnaphthalene; Spirocyclization; Photocycloaddition; Angular triquinane; Photoreaction
• ISSN: 1010-6030; 1873-2666
• DOI: 10.1016/j.jphotochem.2016.01.005

[Display omitted] •Some new polycyclic compounds can be constructed by intramolecular photoreactions.•High-yield synthesis of angular triquinanes is achieved.•Structures of singlet exciplexes govern the modes of the photoreactions. Photoreactions of 4-pentenyl-1-cyanonaphthalenes yield spirocyclic products along with [4+2] cycloadducts. Photoreactions of 5-phenyl derivatives produce a product having tricyclo[6.3.0.01,4]undecadiene skeleton. Formation of angular triquinanes takes place in photoreactions of cycloalkene-linked cyanonaphthalenes. The observation demonstrates that π–π arene ring interactions, steric hindrance, and suitable locations of reaction sites in syn and anti singlet exciplexes govern the modes followed in intramolecular photoreactions of 4-alkenyl-1-cyanonaphthalenes.