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DOI: 10.1039/A606362D (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 2, 1997, 503-508

Nitrate esters in the generation of amino acid radicals

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Christopher J. Easton, Andrew J. Ivory and Craig A. Smith

Abstract

Nitrate esters, prepared by treatment of β-hydroxy-α-amino acid derivatives with nitric acid, react with tributyltin hydride to give the corresponding alkoxyl radicals. These radicals readily undergo β-scission, providing a convenient route for the regiocontrolled production of α-carbon-centred amino acid radicals. By examining the partitioning of the alkoxyl radicals between the β-scission process and the competing hydrogen transfer reaction, it has been possible to evaluate the influence of electronic and steric effects on the β-scission reaction and the formation of the carbon-centred radicals.

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