Adiabatic Intramolecular Hydrogen Atom Transfer in 2-[2-(2-Pyrrolyl)ethenyl]pyridine

Autor: Obi, Masaki, Sakuragi, Hirochika, Arai, Tatsuo
Zdroj: Chemistry Letters; February 1998, Vol. 27 Issue: 2 p169-170, 2p
Abstrakt: 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.
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