Oxidation of methylcyclohexanols by the Pb(OAc)4-LiCl system

Oxidation of methylcyclohexanols by the Pb(OAc)4-LiCl system Full article

Journal

Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science
ISSN: 2376-8444 , E-ISSN: 0568-5230

Output data

Year: 1986, Volume: 35, Number: 11, Pages: 2256-2260 Pages count : 5 DOI: 10.1007/bf00953334

Authors

Kapustina N.I. ¹ , Popkov A.Yu. ¹ , Nikishin G.I. ¹

Affiliations

1	N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow

1. In the reaction of 2-, 3-, and 4-methylcyclohexanols with the Pb(OAc)4,-LiCl oxidizing system, methylcyclohexylalkoxyl radicals are generated, and their formation was confirmed by EPR with the use of a spin trap. 2. The 2- and 4-methylcyclohexylalkoxyl radicals are regioselectively rearranged into 1-methyl- and 3-methyl-5-formylamyl radicals, and the 3-methylcyclohexylalkoxyl radical decomposes in two directions, yielding 2-methyl- and 4-methyl-5-forraylarayl radicals. In the Pb(OAc)4-LiCl system, these radicals are quantitatively oxidized into chloroalkanals. 3. The trans-2 and cis-3-methylcyclohexanols exhibit higher reactivity with respect to the Pb(OAc)4-LiCl system than cis-2 and trans-3-methylcyclohexanols. The reactivity of both isomers of 4-methylcyclohexanol is the same.

Kapustina N.I. , Popkov A.Y. , Nikishin G.I.
Oxidation of methylcyclohexanols by the Pb(OAc)4-LiCl system
Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science. 1986. V.35. N11. P.2256-2260. DOI: 10.1007/bf00953334 OpenAlex

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