Module 1 : Oxidation Reactions

Lecture 10 : Other Nonmetal Oxidants (Dess-Martin, TEMPO and Dioxiranes)

 

 

·      Examples:

A. G. Myers, P. S. Dragovich, J. Am. Chem. Soc. 1992, 114, 5859.

D. A. Evans, J. r. Gage, J. L. Leighton, J. Am. Chem. Soc. 1992, 114, 9434.

M. Mori, T. Tomita, Y. Kita, Tetrahedron Lett. 2004, 45, 4397.

Y.-F. Lu, A. G. Fallis, Tetrahedron Lett. 1993, 34, 3367.

P. A. Wender, S. G. Hegde, R. D. Hubbard, L. Zhang, J. Am. Chem. Soc. 2002, 124, 4956.


1.9.2  2,2,6,6-Tetramethylpiperidin-1-oxyl (TEMPO)


TEMPO is organic heterocyclic compound bearing a radical oxygen atom. This compound was prepared by Lebedev and Kazarnowskii in 1960 from the oxidation of 2,2,6,6-tetramethylpiperidine. In conjunction with other oxidizing agents, this reagent provides mild conditions for oxidations.

TEMPO

F. Montanari, S. Quici, Encyclopedia Reagents for Organic Synthesis, John Wiley and Sons, Inc., L. A. Paquette, Ed., New York, 1995, 7, 4821.