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

R Torriani, M Mella, E Fasani, A Albini

Index: Torriani, Rosangela; Mella, Mariella; Fasani, Elisa; Albini, Angelo Tetrahedron, 1997 , vol. 53, # 7 p. 2573 - 2580

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Citation Number: 12

Abstract

The irradiation of 1, 4-dicyanobenzene (DCB) in the presence of 2, 3-dimethyl-2-butene (DMB) leads to allylation of the aromatic. In the presence of nucleophiles (MeOH, H2O, 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 nucleophiles. The reaction involves ...