Synthetic use of the primary kinetic isotope effect in hydrogen atom transfer: generation of α-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 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.
Wood
Mark E
ME
School of Biosciences, University of Exeter, Geoffrey Pope Building, Stocker Road, Exeter, UKEX4 4QD. m.e.wood@exeter.ac.uk
Bissiriou
Sabine
S
Lowe
Christopher
C
Norrish
Andrew M
AM
Sénéchal
Katell
K
Windeatt
Kim M
KM
Coles
Simon J
SJ
Hursthouse
Michael B
MB
D003903:Deuterium / Q000737:chemistry*; D005609:Free Radicals / Q000737:chemistry*; D006859:Hydrogen / Q000737:chemistry*; D006860:Hydrogen Bonding; D007700:Kinetics; D008958:Models, Molecular
D005609:Free Radicals; D006859:Hydrogen; D003903:Deuterium