Secondary terpene alcohols cis- and trans-verbenol, neo-iso-verbanol, borneol, iso-borneol, and menthol were oxidized by chlorine dioxide into the corresponding ketones. It was shown that the nature of the solvent and catalyst and the structure of the starting compound, including the stereochemistry of the hydroxyl, influenced the oxidation process.
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B. G. Gordon, R. G. Kieffer, and D. H. Rosenblatt, J. Prog. Inorg. Chem., 15, 201 (1972).
O. M. Lezina, S. A. Rubtsova, and A. V. Kuchin, Izv. Akad. Nauk, Ser. Khim., 1779 (2003) [Engl. transl., Russ. Chem. Bull., 8, 1877 (2003)].
A. V. Kuchin, S. A. Rubtsova, and I. V. Loginova, Izv. Akad. Nauk, Ser. Khim., 3, 813 (2001) [Engl. transl., Russ. Chem. Bull., 3, 432 (2001)].
A. V. Kuchin and L. L. Frolova, Izv. Akad. Nauk, Ser. Khim., 1658 (2000) [Engl. transl., Russ. Chem. Bull., 49, 1647 (2000)].
A. V. Kuchin, I. A. Dvornikova, and I. Yu. Nalimova, Izv. Akad. Nauk, Ser. Khim., 2025 (1999) [Engl. transl., Russ. Chem. Bull., 48, 2001 (1999)].
A. V. Kuchin, S. A. Rubtsova, and L. P. Karmanova, Izv. Akad. Nauk, Ser. Khim., 2110 (1998) [Engl. transl., Russ. Chem. Bull., 47, 2051 (1998)].
RF Pat. No. 2,260,580; Byull. Izobret., 26 (2005).
E. S. Suvorkina, Candidate Dissertation in Chemical Sciences, Ufa State Petroleum Technical University, Ufa (2002).
H. C. Brown and C. P. Jang, J. Am. Chem. Soc., 83, 2952 (1961).
C. B. Sharma, Rev. Roum. Chim., 28, 11–12, 967 (1983).
T. Hirao, Chem. Rev., 97, 8, 2707 (1997).
G. A. Tolstikov, Hydroperoxide Oxidation Reactions [in Russian], Nauka, Moscow (1976).
T. A. Tumanova and I. E. Flis, Physico-Chemical Principles of Cellulose Bleaching [in Russian], Lesnaya Promyshlennost´, Moscow (1972), p. 236.
L. L. Frolova, I. V. Dreval´, M. V. Panteleeva, E. U. Ipatova, and A. V. Kuchin, Izv. Akad. Nauk, Ser. Khim., 475 (2003) [Engl. transl., Russ. Chem. Bull., 52, 498 (2003)].
R. Mori, Agric. Biol. Chem., 40, 415 (1976).
RF Pat. No. 2,250,208; Byull. Izobret., 11 (2005).
H. M. Colquhoun, New Pathways for Organic Synthesis: Practical Applications of Transition Metals, Plenum Press, New York (1984).
Acknowledgment
The work was supported by the RF President (Program of Support for Leading Scientific Schools, Grant NSh-4028.2008.3) and the Russian Foundation for Basic Research (Grant No. 05-03-33005).
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Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 585–587, November–December, 2008.
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Frolova, L.L., Popov, A.V., Rubtsova, S.A. et al. Oxidation of secondary terpene alcohols by chlorine dioxide. Chem Nat Compd 44, 724–727 (2008). https://doi.org/10.1007/s10600-009-9190-8
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DOI: https://doi.org/10.1007/s10600-009-9190-8