Journal of Organic Chemistry p. 1077 - 1082 (1981)
Update date:2022-07-30
Topics:
Lewis, Frederick D.
Ho, Tong-Ing
Simpson, J. Thomas
The photochemical addition reactions of seven nonsymmetrical tertiary amines with singlet trans-stilbene are described.Addition of methyldiisopropylamine or isopropyldimethylamine is highly selective for formation of the least substituted α-amino radical, whereas addition of several less highly branched amines is relatively nonselective.The product isotope effect for tert-butylmethyl(trideuteriomethyl)amine is 2.2+/-0.2.Product selectivity is determined by the orientation of the deprotonation of an aminium radical intermediate by the stilbene radical anion.Selectiveoxidation results from e stereoelectronic effect which is most evident w hen one more alkyl group is highly branched.
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