title: Synthetic use of the primary kinetic isotope effect in hydrogen atom transfer 2: generation of captodatively stabilised radicals.
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.
authors.affiliation: Biosciences, College of Life and Environmental Sciences, University of Exeter, Geoffrey Pope Building, Stocker Road, Exeter EX4 4QD, UK. m.e.wood@exeter.ac.uk
authors.forename: Mark E
authors.initials: ME
authors.lastname: Wood
authors.forename: Sabine
authors.initials: S
authors.lastname: Bissiriou
authors.forename: Christopher
authors.initials: C
authors.lastname: Lowe
authors.forename: Kim M
authors.initials: KM
authors.lastname: Windeatt
mesh_terms: D000596:Amino Acids / Q000737:chemistry; D003903:Deuterium / Q000737:chemistry*; D005609:Free Radicals / Q000737:chemistry*; D054879:Halogenation; D006859:Hydrogen / Q000737:chemistry*; D007462:Iodobenzenes / Q000737:chemistry; D007700:Kinetics; D009025:Morpholines / Q000737:chemistry*; D010084:Oxidation-Reduction; D014220:Trialkyltin Compounds / Q000737:chemistry
chemical_list: D000596:Amino Acids; D005609:Free Radicals; D007462:Iodobenzenes; D009025:Morpholines; D014220:Trialkyltin Compounds; C011559:tributyltin; D006859:Hydrogen; C037574:morpholine; D003903:Deuterium