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

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

Organic & biomolecular chemistry (2013-03-13)
Mark E Wood, Sabine Bissiriou, Christopher Lowe, Kim M Windeatt
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.

MATERIALS
Product Number
Brand
Product Description

Supelco
Morpholine, analytical standard
Sigma-Aldrich
Morpholine, purified by redistillation, ≥99.5%
Sigma-Aldrich
Morpholine, ACS reagent, ≥99.0%
Sigma-Aldrich
Morpholine, ReagentPlus®, ≥99%
Sigma-Aldrich
Deuterium, 99.8 atom % D
Sigma-Aldrich
Tributyltin hydride, contains 0.05% BHT as stabilizer, 97%
Sigma-Aldrich
Deuterium, 99.96 atom % D
Sigma-Aldrich
Deuterium, 99.9 atom % D