Photocatalyzed multiple additions of amines to .alpha.,.beta.-unsaturated esters and nitriles

Das, Suresh ; Dileep Kumar, J. S. ; Thomas, George K. ; Shivaramayya, K. ; George, M. V. (1994) Photocatalyzed multiple additions of amines to .alpha.,.beta.-unsaturated esters and nitriles Journal of Organic Chemistry, 59 (3). pp. 628-634. ISSN 0022-3263

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Photoelectron-transfer-catalyzed intermolecular carbon-carbon bond formation of primary, secondary, and tertiary amines with α,β-unsaturated esters and nitriles using photosensitizers such as anthraquinone, acridone, and dicyanoanthracene has been investigated. The addition of a-aminoalkyl radicals, generated via photoelectron-transfer processes, to olefinic substrates and the subsequent 1,5-hydrogen abstraction reactions of the amine-olefin adduct radicals lead to a number of interesting multiple-olefin-added products. The adducts of the primary and secondary amines with a ß-unsaturated esters undergo further cyclizations to give spiro and cyclic lactams, respectively.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society.
ID Code:8852
Deposited On:28 Oct 2010 10:44
Last Modified:31 May 2011 07:18

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