Adiabatic intramolecular hydrogen atom transfer in 2-[2-(2-pyrrolyl)ethenyl]pyridine

被引:27
作者
Obi, M [1 ]
Sakuragi, H [1 ]
Arai, T [1 ]
机构
[1] Univ Tsukuba, Dept Chem, Ibaraki, Osaka 305, Japan
关键词
D O I
10.1246/cl.1998.169
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
2-[2-(2-Pyrrolyl)ethenyl]pyridine (3) forms an intramolecular hydrogen bond between the pyridine and pyrrole ring and undergoes one-way trans --> cis isomerization on direct irradiation. Furthermore, cis isomer undergoes intramolecular hydrogen atom transfer to give a tautomer in the excited singlet state. Based on the experimental findings, effects of intramolecular hydrogen bond and the solvent on the photochemical behaviors of 3 were discussed.
引用
收藏
页码:169 / 170
页数:2
相关论文
共 5 条
[1]   Photochemical behavior of 2-[2-(2-pyridyl) ethenyl] indole on triplet sensitization. Spin multiplicity dependence of the isomerization modes of an intramolecularly hydrogen-bonded compound [J].
Arai, T ;
Obi, M ;
Iwasaki, T ;
Tokumaru, K ;
Lewis, FD .
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 1996, 96 (1-3) :65-69
[2]   NOVEL PHOTOINDUCED HYDROGEN-ATOM TRANSFER THROUGH INTRAMOLECULAR HYDROGEN-BONDING COUPLED WITH CIS-TRANS ISOMERIZATION IN CIS-1-(2-PYRROLYL)-2-(2-QUINOLYL)ETHENE [J].
ARAI, T ;
MORIYAMA, M ;
TOKUMARU, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (07) :3171-3172
[3]   TRANS-]CIS ONE-WAY PHOTOISOMERIZATION OF AN OLEFIN SUBSTITUTED WITH AN INDOLE AND A PYRIDINE RING - EFFECT OF INTRAMOLECULAR HYDROGEN-BOND [J].
ARAI, T ;
IWASAKI, T ;
TOKUMARU, K .
CHEMISTRY LETTERS, 1993, (04) :691-694
[4]   MOLECULAR-STRUCTURE AND PHOTOCHEMISTRY OF (E)-2-(2-(2-PYRIDYL)ETHENYL)INDOLE AND (Z)-2-(2-(2-PYRIDYL)ETHENYL)INDOLE - A CASE OF HYDROGEN-BOND DEPENDENT ONE-WAY PHOTOISOMERIZATION [J].
LEWIS, FD ;
YOON, BA ;
ARAI, T ;
IWASAKI, T ;
TOKUMARU, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (11) :3029-3036
[5]   GENERAL METHOD FOR ALKYLATION AND ALKENYLATION OF HETEROCYCLES [J].
TAYLOR, EC ;
MARTIN, SF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (26) :8095-8102