Journal of Organic Chemistry p. 3953 - 3955 (1985)
Update date:2022-08-04
Topics:
Culp, Sandra J.
Bednar, William M.
Pienta, Norbert J.
Acetonitrile solutions of 1,3-cyclohexadiene or 2,5-dimethyl-2,4-hexadiene and aniline, its N-methylated derivatives, Et2NH, or Et3N were irradiated at 350 nm.Adducts (3-anilinoalkenes) were observed in the presence of the primary or secondary anilines but not with the tertiary aniline or the alkylamines.The products are interpreted as arising via an electron-transfer intermediate within the singlet manifold.The cyclic diene gives competitive <2 + 2> and <4 + 2> dimerization apparently via the triplet.A third diene cyclooctadiene gave no observable chemistry in appreciable amounts.
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