Related Experiment Video
Updated: Jun 23, 2026

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
Published on: June 20, 2014
Oxidation of cyclohexanediol derivatives with 12-tungstophosphoric acid-hydrogen peroxide system
Kango Fujitani1, Toshihiro Mizutani, Tatsuo Oida
1Environment Safety/Quality Assurance Department, New Japan Chemical Co. Ltd., Yagura-cho, Fushimi-ku, Kyoto, Japan. fujitani-k@nj-chem.co.jp
Abstract:
Oxidation of cyclohexanediol derivatives with 12-tungstophospholic acid-hydrogen peroxide system was investigated focusing on a reaction mechanism in the preparation of dicarboxylic acids from olefin because oxidative cleavage of vicinal diols would be a rate-determining step in oxidative cleavage of carbon-carbon double bonds. trans-1,2-Cyclohexanediol (DHC) was converted to adipic acid almost quantatively, while 1-hydroxy-2-methoxycyclohexane (HMC) gave a mixture of adipic acid, glutaric acid and monomethyl adipate. In the case of 1,4-cyclohexanediol, 4-hydroxy-cyclohexanone and many hyperoxidated products were obtained. Based on results for HMC, it is concluded that following route would be also reasonable in oxidative cleavage of vicinal diol with 12-tungstophospholic acid-hydrogen peroxide system: (1) first oxidation of vicinal diol to alpha-hydroxyketone, (2) nucleophilic attack of hydrogen peroxide attacks to carbonyl carbon, (3) Baiyer-Villiger rearrangement of dihydroxy-hydroperoxide to a cyclic ester, (4) hydrolysis and final oxidation to dicarboxylic acid.
Related Concept Videos
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids
Oxidation of Alkenes: Syn Dihydroxylation with Potassium Permanganate
Oxidation of Alcohols
The process of oxidation in a chemical reaction is observed in any of the three forms:
Preparation of Epoxides
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...
Hydroboration-Oxidation of Alkenes

