title: Copper-catalyzed TEMPO addition to propargyl alcohols for the synthesis of vinylic alkoxyamines.
abstract: A variety of vinylic alkoxyamines derived from propargyl alcohols and 2,2,6,6-tetramethylpiperidine N-oxyl (TEMPO) were synthesized in good yields under copper-catalyzed aerobic conditions. A reaction mechanism was proposed, involving the isomerization of propargyl radicals to allenic radicals, and related mechanistic studies were performed. The kinetic isotope effect on the propargyl C-H bond cleavage (α-deprotonation) reaction was observed (kH/kD = 3.76).
authors.affiliation: Department of Energy Systems Research, Ajou University , Suwon 443-749, Korea.
authors.forename: Ye-Won
authors.initials: YW
authors.lastname: Kang
authors.forename: Yoon-Jeong
authors.initials: YJ
authors.lastname: Choi
authors.forename: Hye-Young
authors.initials: HY
authors.lastname: Jang