Photochemical double 5-exo cyclization of alkenyl-substituted dithienylacetylenes: efficient synthesis of diarylated dithienofulvalenes.
Smooth and selective: Upon photoirradiation, bis(3-alkenyl-2-thienyl)acetylenes smoothly and selectively undergo double 5-exo-dig cyclization to produce a series of thiophene-fused pentafulvalenes with various aryl substituents. In this fused π-conjugated skeleton, the fused thiophene rings and the aryl substituents significantly modulate the electronic structure of the pentafulvalene skeleton.
Department of Chemistry, Graduate School of Science, Nagoya University, Furo, Chikusa, Nagoya 464-8602 (Japan) http://orgreact.chem.nagoya-u.ac.jp/en/Home.html. aiko@chem.nagoya-u.ac.jp.
Aiko
A
Fukazawa
Takashi
T
Karasawa
Hongyu
H
Zhang
Kazumitsu
K
Minemura
Cristopher
C
Camacho
Jian
J
Wang
Stephan
S
Irle
Shigehiro
S
Yamaguchi
D000480:Alkynes / Q000737:chemistry*; D001555:Benzene Derivatives / Q000737:chemistry*; D003500:Cyclization; D003517:Cyclopentanes / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D055668:Photochemical Processes; D010777:Photochemistry / Q000379:methods*
D000480:Alkynes; D001555:Benzene Derivatives; D003517:Cyclopentanes; C017332:fulvene
cyclization; pentafulvalene; photoreaction; redox properties; π conjugation