Oxidation of cycloalkanones with hydrogen peroxide: an alternative route to the Baeyer–Villiger reaction. Synthesis of dicarboxylic acid esters

Oxidation of cycloalkanones with hydrogen peroxide: an alternative route to the Baeyer–Villiger reaction. Synthesis of dicarboxylic acid esters Full article

Journal

Tetrahedron
ISSN: 0040-4020 , E-ISSN: 1464-5416

Output data

Year: 2008, Volume: 64, Number: 34, Pages: 7944-7948 Pages count : 5 DOI: 10.1016/j.tet.2008.06.027

Authors

Terent'ev Alexander O. ¹ , Platonov Maxim M. ¹ , Kashin Alexey S. ¹ , Nikishin Gennady I. ¹

Affiliations

1	N.D. Zelinsky Institute of Organic Chemistry, Leninsky Prospect 47, Moscow 119991, Russian Federation

The acid-catalyzed oxidation of cycloalkanones C5–C8 and C12 with hydrogen peroxide in alcohols was performed, and dicarboxylic acid esters were obtained as the major products in 53–70% yields. In the first step, geminal bishydroperoxides are generated from five-to-seven-membered cyclic ketones. The Baeyer–Villiger reaction is a side process accompanied by the formation of ω-hydroxycarboxylic acid esters.

Terent'ev A.O. , Platonov M.M. , Kashin A.S. , Nikishin G.I.
Oxidation of cycloalkanones with hydrogen peroxide: an alternative route to the Baeyer–Villiger reaction. Synthesis of dicarboxylic acid esters
Tetrahedron. 2008. V.64. N34. P.7944-7948. DOI: 10.1016/j.tet.2008.06.027 WOS Scopus OpenAlex

≡ Web of science:	WOS:000258271300012
≡ Scopus:	2-s2.0-46649089897
≡ OpenAlex:	W1980759477