TRANSFORMATIONS OF PEROXIDE OZONOLYSIS PRODUCTS
1675
Table 1. Ozonolysis of α-pinene (1) and 3-carene (2) in different solvents, followed by treatment with 4-hydroxybenzo-
hydrazide (3)
Terpene
Solvent
Methanol
Product
Yield, %
86
1
1
1
2
2
2
6
8
8
7
9
9
Methylene chloride
Tetrahydrofuran
Methanol
89
54
72
Methylene chloride
Tetrahydrofuran
76
78
keto ester 7 from 3-carene (2). The IR and NMR spec-
tra of 6 and 7 were identical to those reported in [11].
FUNDING
This study was financially supported by the program
“Fundamentals of Chemistry” of the Russian Academy of
Sciences (project no. 8, “Chemo-, Regio-, and Stereoselec-
tive Transformations of Terpenoids, Steroids, and Lipids in
Target-Oriented Synthesis of Low-Molecular-Weight Bio-
regulators,” state registry no. AAAA-A17-117011910023-
2, 2017).
Methyl 2-[(1R,3R)-3-acetyl-2,2-dimethylcyclo-
butyl]acetate (6). Rf 0.44 (hexane–methyl tert-butyl
ether, 2:1), [α]D20 = –24.8° (c = 0.73, CH2Cl2).
Methyl 2-[(1S,3R)-2,2-dimethyl-3-(2-oxopropyl)-
cyclopropyl]acetate (7). Rf 0.42 (hexane–methyl tert-
butyl ether, 2:1), [α]D20 = –19.9 (c = 16.50, CH2Cl2).
In the reaction in methylene chloride we isolated
0.61 g (89%) of keto acid 8 from α-pinene (1) and
0.52 g (76%) of keto acid 9 from 3-carene (2). In the
reaction in tetrahydrofuran we isolated 0.37 g (54%) of
8 and 0.49 g (72%) of 9 from terpenes 1 and 2,
respectively.
CONFLICT OF INTEREST
The authors declare no conflict of interest.
REFERENCES
1. Plemenkov, V.V., Khim. Rastit. Syr’ya, 2006, no. 3, p. 55.
2-[(1R,3R)-(3-Acetyl-2,2-dimethylcyclobutyl)]-
acetic acid (8). Rf 0.21 (hexane–methyl tert-butyl
ether, 4:1), [α]D20 = –39.8° (c = 0.82, CH2Cl2).
2. Frolova, L.L., Bezuglaya, L.V., Popov, A.V.,
Kuchin, A.V., and Vendilo, N.V., Izv. Komi Nauch. Tsentra
Ural. Otd. Ross. Akad. Nauk, 2012, no. 1, p. 11.
2-[(1R,3S)-(2,2-Dimethyl-3-(2-oxopropyl)cyclo-
propyl)]acetic acid (9). Rf 0.19 (hexane–methyl tert-
butyl ether, 4:1), [α]D20 = –14° (c = 2.23, CH2Cl2).
3. Shaderkina, V.A. and Shaderkin, I.A., Eksp. Klin. Urolog.,
2019, no. 1, p. 77.
The IR and NMR spectra of 8 and 9 were identical
to those given in [12].
4. Van Ornum, S.G., Champeau, R.M., and Pariza, R., Chem.
Rev., 2006, vol. 106, p. 2990.
The IR spectra were recorded from thin films on
a Shimadzu IR Prestige-21 Fourier transform spec-
trometer. The NMR spectra were run on a Bruker
Avance III 500 spectrometer at 500.13 MHz for 1H and
125.76 MHz for 13C, using CDCl3 as solvent and
tetramethylsilane as internal standard. The optical
rotations were measured on a Perkin Elmer 241-MC
polarimeter. Analytical TLC was performed on Sorbfil
silica gel plates (Russia).
5. Ishmuratov, G.Yu., Legostaeva, Yu.V., Garifullina, L.R.,
Botsman, L.P., Yakovleva, M.P., and Tolstikov, G.A.,
Chem. Nat. Compd., 2015, vol. 51, p. 199.
6. Ishmuratov, G.Yu., Legostaeva, Yu.V., Botsman, L.P.,
and Tolstikov, G.A., Russ. J. Org. Chem., 2010, vol. 46,
p. 1593.
7. Myasoedova, Yu.V., Nazarov, I.S., and Ishmuratov, G.Yu.,
Russ. J. Org. Chem., 2019, vol. 55, p. 47.
ACKNOWLEDGMENTS
https://doi.org/10.1134/S107042801901007X
8. Legostaeva, Yu.V., Garifullina, L.R., Nazarov, I.S.,
Kravchenko, A.A., Ishmuratova, N.M., and Ishmura-
tov, G.Yu., Chem. Nat. Compd., 2017, vol. 53, p. 891.
This study was performed using the facilities of the
Chemistry joint center (Ufa Institute of Chemistry, Ufa
Federal Research Center, Russian Academy of Sciences).
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 56 No. 9 2020