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Issue 20, 2010
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Synthetic use of the primary kinetic isotope effect in hydrogen atom transfer: generation of α-aminoalkyl radicals

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Abstract

The extent to which deuterium can act as a protecting group to prevent unwanted 1,5-hydrogen atom transfer to aryl and vinyl radical intermediates was examined in the context of the generation of α-aminoalkyl radicals in a pyrrolidine ring. Intra- and intermolecular radical trapping following hydrogen atom transfer provides an illustration of the use of the primary kinetic isotope effect in directing the outcome of synthetic C–C bond-forming processes.

Graphical abstract: Synthetic use of the primary kinetic isotope effect in hydrogen atom transfer: generation of α-aminoalkyl radicals

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Article information


Submitted
04 Jun 2010
Accepted
05 Jul 2010
First published
17 Aug 2010

Org. Biomol. Chem., 2010,8, 4653-4665
Article type
Paper

Synthetic use of the primary kinetic isotope effect in hydrogen atom transfer: generation of α-aminoalkyl radicals

M. E. Wood, S. Bissiriou, C. Lowe, A. M. Norrish, K. Sénéchal, K. M. Windeatt, S. J. Coles and M. B. Hursthouse, Org. Biomol. Chem., 2010, 8, 4653
DOI: 10.1039/C0OB00205D

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