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On the mechanism of the photochemical reaction between 1,4-dicyanobenzene and 2,3-dimethylbutene in the presence of nucleophiles

✍ Scribed by Rosangela Torriani; Mariella Mella; Elisa Fasani; Angelo Albini

Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
424 KB
Volume
53
Category
Article
ISSN
0040-4020

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✦ Synopsis

The irradiation of 1,4-dicyanobenzene (DCB) in the presence of 2,3dimethyl-2-butene (DMB) leads to allylation of the aromatic. In the presence of nucleophiles (MeOH, H20, CF3CH2OH ) this reaction is substituted by the nucleophile olefin combination -aromatic substitution (NOCAS) process. The quantum yield increases from 0.006 in the absence to a limiting value of ca 0.02 in the presence of the nueleophiles. The reaction involves competing deprotonation and nucleophile addition to the olefin radical cation, followed by coupling of the thus formed radical with DCB -.. Minor processes are hydrogen abstraction from the solvent by the allyl radical, revealed by isolation of the phenylpentanonitrile 3 and coupling of the radical ions before separation, revealed by a small amount of the cyclohexadiene 6.

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