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Issue 16, 2013
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Synthetic use of the primary kinetic isotope effect in hydrogen atom transfer 2: generation of captodatively stabilised radicals

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Abstract

Using C-3 di-deuterated morpholin-2-ones bearing N-2-iodobenzyl and N-3-bromobut-3-enyl radical generating groups, only products derived from the more stabilised C-3, rather than the less stabilised C-5 translocated radicals, were formed after intramolecular 1,5-hydrogen atom transfer, suggesting that any kinetic isotope effect present was not sufficient to offset captodative stabilisation.

Graphical abstract: Synthetic use of the primary kinetic isotope effect in hydrogen atom transfer 2: generation of captodatively stabilised radicals

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Publication details

The article was received on 06 Feb 2013, accepted on 04 Mar 2013 and first published on 05 Mar 2013


Article type: Paper
DOI: 10.1039/C3OB40275D
Citation: Org. Biomol. Chem., 2013,11, 2712-2723
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    Synthetic use of the primary kinetic isotope effect in hydrogen atom transfer 2: generation of captodatively stabilised radicals

    M. E. Wood, S. Bissiriou, C. Lowe and K. M. Windeatt, Org. Biomol. Chem., 2013, 11, 2712
    DOI: 10.1039/C3OB40275D

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