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Photochemical monoalkylation of propanedinitrile by electron-rich alkenes.


PMID 18537243

Abstract

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.

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344311
2,5-Dimethyl-2,4-hexadiene, 96%
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