Photochemical Monoalkylation of Propanedinitrile by Electron-Rich Alkenes

The synthesis of monoalkylated propanedinitriles was achieved upon photoirradiation of MeCN/H2O 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 (electr...

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Bibliographic Details
Published inOrganic letters Vol. 10; no. 13; pp. 2741 - 2743
Main Authors Ohashi, Maki, Nakatani, Keisuke, Maeda, Hajime, Mizuno, Kazuhiko
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 03.07.2008
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ORGANIC-CHEMISTRY
ALPHA-CYANO ESTERS
DIPOLAR APROTIC MEDIA
RADICAL IONS
MALONONITRILE
SYNTHETIC APPLICATIONS
MALONATE ESTERS
BETA-KETO-ESTERS
DEFICIENT ALKENES
DEALKOXYCARBONYLATIONS
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Summary:The synthesis of monoalkylated propanedinitriles was achieved upon photoirradiation of MeCN/H2O 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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol800862x