Diffusion Controlled Hydrogen Atom Abstraction from Tertiary Amines by the Benzyloxyl Radical. The Importance of C− H/N Hydrogen Bonding

M Salamone, G Anastasi, M Bietti, GA DiLabio

Index: Salamone, Michela; Anastasi, Gloria; Bietti, Massimo; Dilabio, Gino A. Organic Letters, 2011 , vol. 13, # 2 p. 260 - 263

Full Text: HTML

Citation Number: 16

Abstract

The rate constants for H-atom abstraction (k H) from 1, 4-cyclohexadiene (CHD), triethylamine (TEA), triisobutylamine (TIBA), and DABCO by the cumyloxyl (CumO•) and benzyloxyl (BnO•) radicals were measured. Comparable k H values for the two radicals were obtained in their reactions with CHD and TIBA whereas large increases in k H for TEA and DABCO were found on going from CumO• to BnO•. These differences are attributed to the ...