Synthetic use of the primary kinetic isotope effect in hydrogen atom transfer: generation of ?-aminoalkyl radicals
Synthetic use of the primary kinetic isotope effect in hydrogen atom transfer: generation of ?-aminoalkyl radicals
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 alpha-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.
4653-4665
Wood, Mark E.
790e32fe-abef-42ca-b663-a23d8276e1e2
Bissiriou, Sabine
2861c436-298f-4d53-ad0d-2e089207a252
Lowe, Christopher
be61664a-b33e-4526-b98e-91c028ce4d5c
Norrish, Andrew M.
fdfeca72-a698-4b06-a7c7-8c8079cc00c7
Sénéchal, Katell
42b7c6ec-ac92-4acc-8304-0d9dd99688bb
Windeatt, Kim M.
6f623724-0827-467b-a50e-d74df1cfff80
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
2010
Wood, Mark E.
790e32fe-abef-42ca-b663-a23d8276e1e2
Bissiriou, Sabine
2861c436-298f-4d53-ad0d-2e089207a252
Lowe, Christopher
be61664a-b33e-4526-b98e-91c028ce4d5c
Norrish, Andrew M.
fdfeca72-a698-4b06-a7c7-8c8079cc00c7
Sénéchal, Katell
42b7c6ec-ac92-4acc-8304-0d9dd99688bb
Windeatt, Kim M.
6f623724-0827-467b-a50e-d74df1cfff80
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Wood, Mark E., Bissiriou, Sabine, Lowe, Christopher, Norrish, Andrew M., Sénéchal, Katell, Windeatt, Kim M., Coles, Simon J. and Hursthouse, Michael B.
(2010)
Synthetic use of the primary kinetic isotope effect in hydrogen atom transfer: generation of ?-aminoalkyl radicals.
Organic & Biomolecular Chemistry, 8 (20), .
(doi:10.1039/c0ob00205d).
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 alpha-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.
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e-pub ahead of print date: 17 August 2010
Published date: 2010
Organisations:
Organic Chemistry: Synthesis, Catalysis and Flow
Identifiers
Local EPrints ID: 346223
URI: http://eprints.soton.ac.uk/id/eprint/346223
ISSN: 1477-0520
PURE UUID: 771aac53-7b7d-4e21-b35a-9649742f0658
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Date deposited: 18 Dec 2012 11:44
Last modified: 15 Mar 2024 03:01
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Contributors
Author:
Mark E. Wood
Author:
Sabine Bissiriou
Author:
Christopher Lowe
Author:
Andrew M. Norrish
Author:
Katell Sénéchal
Author:
Kim M. Windeatt
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