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The chemistry of polycyclic arene imines. II. Photochemistry of phenanthrene 9,10‐imine and of its N ‐butyl derivative
Author(s) -
Weitzberg Moshe,
Avnir David,
Aizenshtat Zeev,
Blum Jochanan
Publication year - 1983
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570200435
Subject(s) - chemistry , phenanthrene , imine , dichloromethane , oxazole , medicinal chemistry , photochemistry , organic chemistry , catalysis , solvent
The uv irradiation of phenanthrene 9, 10‐imine has been shown to give 9 H ‐tetrabenzo[ a, c, g, i ]carbazole as the major photo‐product both in argon purged acetone and in dichloromethane. Phenanthrazine, N ‐9‐phenanthrenyl‐9‐phenanthrenamine and phenanthrene were formed in smaller quantities. 9‐Phenanthrenamine was found to be a minor by‐product. N ‐Butylphenanthrene 9, 10‐imine yielded under similar conditions phenanthrene and N ‐butyl‐9‐phenanthrenamine as the only isolable polycyclic compounds. In the presence of air the substituted imine gave mainly 2‐propylphenanthro[9, 10‐ d ]oxazole.