Tetrahedron letters

Radical oxidation of amides and related compounds with hypervalent tert-butylperoxyiodanes: Synthesis of imides and tert-butylperoxyamide acetals

M Ochiai, D Kajishima, T Sueda

Index: Ochiai, Masahito; Kajishima, Daisuke; Sueda, Takuya Tetrahedron Letters, 1999 , vol. 40, # 30 p. 5541 - 5544

Full Text: HTML

Citation Number: 36

Abstract

tert-Butylperoxyiodane undergoes oxidation of the methylene groups α to the nitrogen atom of amides (or carbamates) yielding imides or tert-butylperoxyamide acetals, depending on the reaction conditions. A proposed mechanism involves generation of carbon-centered radicals α to the nitrogen atom.

Related Articles:

A facile approach to trans-4, 5-pyrrolidine lactam and application in the synthesis of nemonapride and streptopyrrolidine

[Huang, Wei; Ma, Jing-Yi; Yuan, Mu; Xu, Long-Fei; Wei, Bang-Guo Tetrahedron, 2011 , vol. 67, # 40 p. 7829 - 7837]

Biomimetic aerobic oxidation of amino alcohols to lactams

[Babu, Beneesh P.; Endo, Yoshinori; Baeckvall, Jan-E. Chemistry--A European Journal, 2012 , vol. 18, # 37 p. 11524 - 11527,4]

Syntheses of phosphonic esters of alendronate, pamidronate and neridronate

[Guenin, Erwann; Monteil, Maelle; Bouchemal, Nadia; Prange, Thierry; Lecouvey, Marc European Journal of Organic Chemistry, 2007 , # 20 p. 3380 - 3391]

More Articles...