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One‐Step Synthesis of Benzotetra‐ and Benzopentacyclic Compounds through Intramolecular [2+3] Photocycloaddition of Alkenes to Naphthalene
Author(s) -
Mukae Hirofumi,
Maeda Hajime,
Mizuno Kazuhiko
Publication year - 2006
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200602553
Subject(s) - intramolecular force , naphthalene , acetonitrile , chemistry , alkene , photochemistry , adduct , irradiation , medicinal chemistry , stereochemistry , organic chemistry , physics , catalysis , nuclear physics
Rings from light : Irradiation of acetonitrile solutions containing 1‐cyano‐2‐(4‐pentenyl)naphthalene derivatives afforded benzotetra‐ and benzopentacyclic compounds with tri‐ and tetraquinane skeletons in high yields, through intramolecular [2+3] photocycloaddition of the alkene at the 2,4‐positions of the cyanonaphthalene (see scheme; n =1, 2). The structures of these adducts were confirmed by their spectral properties and by X‐ray crystallographic analyses.