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Intramolecular Photocyclization of ω, ω‐Diphenyl‐(ω−1)‐alken‐1‐ols by an Exciplex Quenching Mechanism
Author(s) -
Mizuno Kazuhiko,
Tamai Toshiyuki,
Nishiyama Toshinori,
Tani Kyoko,
Sawasaki Mayumi,
Otsuji Yoshio
Publication year - 1994
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199421131
Subject(s) - excimer , intramolecular force , photochemistry , alkene , chemistry , quenching (fluorescence) , benzene , mechanism (biology) , reaction mechanism , medicinal chemistry , stereochemistry , organic chemistry , fluorescence , catalysis , physics , quantum mechanics , philosophy , epistemology
In the 9,10‐anthracenedicarbonitrile‐sensitized irradiation of the title compounds 1a–f in benzene, the photocyclization of 1b–d leads efficiently to products 2b–d with five‐, six‐, and seven‐membered rings, respectively (A = 9,10‐anthracenedicarbonitrile). This cyclization is also possible with 3‐substituted derivatives of 1c . The reaction proceeds via an exciplex of the sensitizer A and alkene 1 .