Issue 20, 2010

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

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

Supplementary files

Article information

Article type
Paper
Submitted
04 Jun 2010
Accepted
05 Jul 2010
First published
17 Aug 2010

Org. Biomol. Chem., 2010,8, 4653-4665

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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