Photochemical monoalkylation of propanedinitrile by electron-rich alkenes.
The synthesis of monoalkylated propanedinitriles was achieved upon photoirradiation of MeCN/H(2)O solutions containing propanedinitrile (1; malononitrile) and electron-rich alkenes in the presence of lithium carbonate and a catalytic amount of 9-cyanophenanthrene or redox-type photosensitizers (electron-mediating photosensitizers), through regioselective anti-Markovnikov photochemical polar addition of 1 into electron-rich alkenes. With 2,5-dimethyl-2,4-hexadiene (2g) as an electron-rich alkene, propanedinitrile-incorporated dimer 4g was obtained.
Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, 1-1 Gakuen-cho, Naka-ku, Sakai, Osaka 599-8531, Japan.
Maki
M
Ohashi
Keisuke
K
Nakatani
Hajime
H
Maeda
Kazuhiko
K
Mizuno