Reactions of terpene alcohols and diols with chlorine dioxide in dimethylformamide

L. L. Frolova; A. V. Popov; L. V. Bezuglaya; I. N. Alekseev; P. A. Slepukhin; A. V. Kutchin

doi:10.1134/S107036321603018X

Reactions of terpene alcohols and diols with chlorine dioxide in dimethylformamide

Authors: Frolova L.L.¹, Popov A.V.¹, Bezuglaya L.V.¹, Alekseev I.N.¹, Slepukhin P.A.²^,3, Kutchin A.V.¹
Affiliations:
1. Institute of Chemistry, Komi Research Center
2. Postovskii Institute of Organic Synthesis
3. Yeltsin Ural Federal University
Issue: Vol 86, No 3 (2016)
Pages: 613-621
Section: Article
URL: https://journals.rcsi.science/1070-3632/article/view/214253
DOI: https://doi.org/10.1134/S107036321603018X
ID: 214253

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Abstract

The system chlorine dioxide–dimethylformamide in combination with or without a catalytic amount of MoCl₅, CeCl₃, ZrOCl₂, or VO(acac)₂ induces oxidative chlorination of a number of bicyclic terpene alcohols and vicinal diols. 2α-Chloropinan-3-one, 3α-chloro-10β-pinan-4-one, 5α-chloro-3α-hydroxycaran-4-one, 5β-chloro-3β-hydroxycaran-4-one, and 4α-chloro-2α-hydroxypinan-3-one were thus synthesized in good preparative yields.