Synthesis of Amino Alcohols of the Cyclododecane and Decahydro-1,4-ethanonaphthalene Series

Article abstract of DOI:10.1134/S1070428020060068

Abstract: 2-Aminocyclododecan-1-ol and 6(3)-aminodecahydro-1,4-ethanonaphthalen-5(2)-ols (mixture of isomers) were synthesized in two steps via oxidative hydroxybromination of cyclododecene and 1,2,3,4,4a,5,6,8a(1,4,4a,5,6,7,8,8a)-octahydro-1,4-ethanonaph

Full text of DOI:10.1134/S1070428020060068

ISSN 1070-4280, Russian Journal of Organic Chemistry, 2020, Vol. 56, No. 6, pp. 1001–1005. © Pleiades Publishing, Ltd., 2020.
Russian Text © The Author(s), 2020, published in Zhurnal Organicheskoi Khimii, 2020, Vol. 56, No. 6, pp. 893–899.
Synthesis of Amino Alcohols of the Cyclododecane
and Decahydro-1,4-ethanonaphthalene Series
O. A. Sadigova,*, H. M. Alimardanova, Sh. I. Ismailovaa, and N. R. Babayeva
a Mamedaliev Institute of Petrochemical Processes, National Academy of Sciences of Azerbaijan, Baku, 1025 Azerbaijan
*e-mail: omar.sadiqov@gmail.com
Received January 23, 2020; revised March 5, 2020; accepted March 16, 2020
Abstract—2-Aminocyclododecan-1-ol and 6(3)-aminodecahydro-1,4-ethanonaphthalen-5(2)-ols (mixture of
isomers) were synthesized in two steps via oxidative hydroxybromination of cyclododecene and
1,2,3,4,4a,5,6,8a(1,4,4a,5,6,7,8,8a)-octahydro-1,4-ethanonaphthalines with the system hydrogen peroxide–HBr.
In the first step, oxidation of hydrogen bromide with hydrogen peroxide generated intermediate dioxidanium
bromide which added to the C=C double bond of the unsaturated substrate to give the corresponding α-bromo
alcohols. In the second step, substitution of the bromine atom by amino group in the presence of an alkali
afforded α-amino alcohols.
Keywords: cyclododecene, tricyclododecene, aminocyclododecanol, hydrobromic acid, hydrogen peroxide,
primary and secondary amines, aminooctrahydro-1,4-ethanonaphthol
DOI: 10.1134/S1070428020060068
Preparation of polyfunctional C5–C12-alicyclic com-
pounds is of great interest due to broad spectrum of
their application in petrochemical and organic syn-
thesis. These compounds are important not only per se
but also as intermediate products in the synthesis of
biologically active and pharmacological agents [1–9],
corrosion inhibitors, and antioxidants [9, 10]. Among
them, of particular importance are macrocyclic and
bridged amino alcohols and their derivatives [11–14].
Introduction of hydrophilic amino and hydroxy groups
into a hydrophobic carbon macrocycle could signif-
icantly change their biological and pharmacological
activity [9, 12]. A number of synthetic analogs of
various natural biologically active compounds, as well
as of antiviral and antibacterial agents [9, 11, 12], have
been designed on the basis of macrocyclic amino
alcohols [3].
unsaturated cyclic C12-hydrocarbons, namely cyclo-
dodecene and 1,2,3,4,4a,5,6,8a-octahydro-1,4-ethano-
naphthalene, using the system H2O2–HBr.
We previously reported the results of studies on the
synthesis of vicinal amino alcohols based on cyclo-
hexene and bicyclo[2.2.1]hept-2-ene derivatives
[16, 20] via addition of intermediate oxidizing species
generated in situ to the C=C double bond and subse-
quent substitution of halogen by the action of a primary
or secondary amine. In continuation of these studies, in
this work we tried to synthesize amino alcohols from
macro- and polycyclic hydrocarbons.
The starting materials were cyclododecene (1) and
a mixture of isomeric 1,2,3,4,4a,5,6,8a- (2A) and
1,4,4a,5,6,7,8,8a-octahydro-1,4-ethanonaphthalenes
(2B) which was obtained by partial hydrogenation of
1,4,4a,5,6,8a-hexahydro-1,4-ethanonaphthalene over
nickel–kieselguhr catalyst according to [21]. We have
found that both cyclododecene (1) and isomer mixture
2A/2B reacted with the system H2O2–HBr under mild
conditions (20–50°C) to give the corresponding
α-bromo alcohols 3 and 4 (A/B) via addition of a meta-
stable complex generated in situ from hydrogen per-
oxide and hydrogen bromide. The yield of 3 and 4
increased as the temperature rose from 20 to 50°C and
reached 59.3–84.6%. Further raising the temperature to
The most common method for the synthesis of
various amino alcohols is ring opening of oxiranes by
the action of nitrogen nucleophiles [4, 9–15]. Published
data on macrocyclic and bridged amino alcohols are
few in number [16–19], and the available information
refers mainly to heterocyclic derivatives [7, 12].
The present study was aimed as synthesizing
macrocyclic and bridged polycyclic amino alcohols
from products of oxidative hydroxybromination of
1001

SADIGOV et al.
1002
Scheme 1.
Br–
H
H
H
O
HBr
1, 2
H
O
O
H
H
O
H
O
H
H2O2
Br–
O
HBr
H
H
C
Br+
O
H
H
H
H
H
H
H
OH
Br
O
–H2O
H
Br+
3, 4 (A, B)
1, Cyclododecene; 2, 1,2,3,4,4a,5,6,8a- and 1,4,4a,5,6,7,8,8a-octahydro-1,4-ethanonaphthalenes (mixture of isomers); 3, 2-bromo-
cyclododean-1-ol; 4, 6-bromodecahydro-1,4-ethanonaphthalen-5-ol (A) and 3-bromodecahydro-1,4-ethanonaphthalen-2-ol (B)
(mixture of isomers).
75°C promoted decomposition of hydrogen peroxide
and intermediate complex with liberation of molecular
oxygen and/or bromine, respectively.
GLC analyses were run on a Tsvet-500 chromatograph
equipped with a thermal conductivity detector and
a 2000×4-mm column packed with 10% poly(ethylene
glycol succinate) on Chromosorb W; carrier gas He,
flow rate 40 cm3/min; oven temperature 150°C.
Scheme 1 shows a plausible mechanism for the
formation of cyclic α-bromo alcohols from cyclic
olefins in the system H2O2–HBr. The attack of hydro-
gen bromide molecule on the oxygen atom of hydrogen
peroxide give intermediate complex C containing
electrophilic oxygen. The addition of this complex to
C=C double bond of the substrate is followed by
elimination of water and energetically favorable charge
redistribution with the generation of active hydroxy
bromide intermediate. Fast addition of electrophilic
oxygen to the double bond gives carbocation which
then reacts with bromide ion to produce hydroxy
bromide. Presumably, the addition of electrophilic oxy-
gen is controlled by structural conformational direc-
tionality in a way similar to nucleophilic oxirane ring
opening according to the Fürst–Plattner rule [12, 13].
Butylamine, diethylamine, piperidine, morpholine,
hydrogen peroxide, aqueous HBr, and cyclododecene
(1:1 mixture of cis and trans isomers) were commercial
products purchased from Alfa Aesar or Johnson
Matthey PLC; a mixture of 1,2,3,4,4a,5,6,8a-octahy-
dro-1,4-ethanonaphthalene (2A) and 1,4,4a,5,6,7,8,8a-
octahydro-1,4-ethanonaphthalene (2B) (92.5:7.5) was
obtained by partial hydrogenation of 1,4,4a,5,6,8a-
hexahydro-1,4-ethanonaphthalene over nickel–kiesel-
guhr according to the procedure reported in [5, 16].
General procedure for the hydroxybromination
of C12-cycloolefins [16, 19]. A flask was charged at
a required temperature with 0.15–0.2 mol of 8–15%
aqueous HBr and 0.1 mol of substrate 1 or 2, and 0.2–
0.25 mol of 26–30% aqueous hydrogen peroxide was
added at a rate of 10 g/h from a dropping funnel with
vigorous stirring (200–250 rpm). The mixture was
stirred for 5–6 h until the oxidant was consumed com-
pletely according to the data of permanganometric and
iodometric titration. The organic layer was separated,
the aqueous layer was extracted with toluene (2×
100 mL), the extracts were combined with the organic
phase, treated with a 10% aqueous solution of Na2CO3,
and dried over magnesium sulfate, and the solvent
was removed under reduced pressure.
By reacting bromo alcohols 3 and 4 with primary
and secondary amines we obtained amino alcohols 5a–
5d and 6a–6d (Scheme 2).
EXPERIMENTAL
The IR spectra were recorded in the range 400–
4000 cm–1 on a Bruker Alpha FT-IR spectrometer from
samples dispersed in mineral oil or pressed with KBr.
1
The H and 13C NMR spectra were measured on
a Bruker 300 instrument at 300.18 and 75 MHz, respec-
tively, using chloroform-d as solvent and reference
(δ 7.25, δC 77.00 ppm). Elemental analysis was per-
formed on a Leco TruSpec Micro analyzer (USA).
2-Bromocyclododecan-1-ol (3) was synthesized
from 4.98 g (30 mmol) of cyclododecene. Yield 6.49 g
(82.3%), cis/trans ratio 35:65, bp 207–209°C
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 56 No. 6 2020

SYNTHESIS OF AMINO ALCOHOLS
1003
Scheme 2.
OH
NR1R2
( )7
OH–
3, 4
+
HNR1R2
5a–5d
–HBr
OH
NR1R2
OH
NR1R2
+
6a–6d
6'a–6'd
5, 6, R1 = R2 = Et (a); R1 = Н, R2 = Bu (b); R1R2N = piperidin-1-yl (c), morpholin-4-yl (d).
(0.204 kPa). IR spectrum, ν, cm–1: 3495 (OH), 2860–
2855 (CH2, sym.), 1460 (δCH2, asym.), 1360, 1345
(δCH), 1128 (δOH), 765, 750 (C–Br) [22]. H NMR
filtered off, washed with propan-2-ol, dried, and recrys-
tallized from propan-2-ol–water (5:1).
1
2-(Diethylamino)cyclododecan-1-ol (5a) was
synthesized from 6.57 g (25 mmol) of 3 and 3.3 g
(45 mmol) of diethylamine. Yield 5.5 g (86.3%),
cis/trans 45:55, mp 71–73°C. IR spectrum, ν, cm–1:
3496 (OH), 3340, 3236 (NH), 2960 (CH3, sym.), 2855
(CH2, sym.), 1295 (C–N), 1460 (δCH2, asym.), 1096
spectrum, δ, ppm: 1.31–1.73 m (20H, CH2), 3.57 t (1H,
CHOH, J = 7.9 Hz), 3.58 br.s (1H, OH), 3.67 t (1H,
13
CHBr, J = 7.9 Hz). C NMR spectrum, δC, ppm: 78.2
(C1), 47.4 (C2), 32.8 (C3), 30.8 (C12), 24.8 (C6–C10),
23.8 (C5), 23.6 (C11), 21 (C4) [23]. Found, %: C 54.25;
H 8.23; Br 30.18. C12H23BrO. Calculated, %: C 54.75;
H 8.74; Br 30.42.
1
(δOH). H NMR spectrum, δ, ppm: 1.05 t [6H,
N(CH2CH3)2, J = 8.2 Hz], 1.26–1.58 m (20H, CH2),
2.42 d [4H, N(CH2)2, J = 8.1 Hz], 2.70 t (1H, CHN, J =
8.0 Hz), 3.46 d (1H, CHOH, J = 8.1 Hz), 3.58 br.s (1H,
OH). 13C NMR spectrum, δC, ppm: 74.2 (C1), 70.6
(C2), 50.3 (NCH2), 30.2 (C12), 28.7 (C3), 24.6 (C5–
C11), 13.8 (CH3). Found, %: C 74.88; H 12.56; N 5.24.
C16H33NO. Calculated, %: C 75.29; H 12.94; N 5.49.
6-Bromodecahydro-1,4-ethanonaphthalen-5-ol
(4A) and 3-bromodecahydro-1,4-ethanonaphthalen-
2-ol (4B) were synthesized from 5.67 g (35 mmol) of
isomer mixture A/B. Yield 7.14 g (78.8%), ratio 4A/4B
92.6:7.4, mp 101–103°C. IR spectrum, ν, cm–1: 3495
(OH), 2860–2855 (CH2, sym.), 1460 (δCH2, asym.),
1360, 1345 (δCH), 1095 (δOH), 765, 750 (C–Br).
1H NMR spectrum, δ, ppm: 1.30–1.78 m (16H, CH2),
3.49 d (1H, CHBr, J = 7.3 Hz), 3.59 d (1H, HCOH, J =
7.2 Hz), 3.65 br.s (1H, OH). 13C NMR spectrum, δC,
ppm: 75.6 (C6), 57 (C4), 42.8 (C9), 41.8 (C5), 31.3 (C7),
27.9 (C10), 26.5 (C7), 25.0 (C3), 24.5 (C1, C11), 23.8
(C2, C12). Found, %: C 54.87; H 6.98; Br 30.68.
C12H19BrO. Calculated, %: C 55.38; H 7.69; Br 30.77.
2-(Butylamino)cyclododecan-1-ol (5b) was
synthesized from 6.57 g (25 mmol) of 3 and 3.65 g
(50 mmol) of butan-1-amine. Yield 4.7 g (73.8%),
cis/trans 45:55, mp 90–93°C. IR spectrum, ν, cm–1:
3496 (OH), 3240 (NH), 1665 (C–N), 1460 (δCH2,
1
asym.), 1450 (δCH), 1110 (δOH). H NMR spectrum,
δ, ppm: 0.94 t (3H, CH3, J = 6.8 Hz), 1.27–1.46 m
(24H, CH2), 2.10 br.s (1H, NH), 2.57 d (2H, NCH2, J =
7.2 Hz), 2.71 d (1H, CHN, J = 7.9 Hz), 3.47 t (1H,
CHOH, J = 8.1 Hz), 3.63 br.s (1H, OH). 13C NMR
spectrum, δC, ppm: 76.4 (C1), 63.8 (C2), 30.8 (C3), 29.8
(C12), 24.6 (C5–C10), 24.3 (C11), 24 (C4), 50.4 (C1),
24 (CH2), 11.7 (CH3). Found, %: C 74.85; H 12.12;
N 5.21. C16H33NO. Calculated, %: C 75.29; H 12.41;
N 5.49.
General procedure for the reaction of compounds
3 and 4 with amines. A 40% solution of potassium
hydroxide in propan-2-ol or a solution of K2CO3 in
chloroform, 30–50 mL, was added to 6.57 g (25 mmol)
of compound 3 or 6.48 g (25 mmol) of 4. The mixture
was heated to 50–60°C, and 0.15–0.25 mmol of the
corresponding amine was added dropwise with stirring
over a period of 1–1.5 h. The mixture was stirred for
3–6 h at that temperature until the initial compound
(3 or 4) disappeared completely according to the GLC
and TL data. Liquid products were washed until neutral
reaction (litmus), dried over MgSO4, and distilled
under reduced pressure. Crystalline products were
2-(Piperidin-1-yl)cyclododecan-1-ol (5c) was
synthesized from 6.57 g (25 mmol) of 3 and 4.25 g
(50 mmol) of piperidine. Yield 4.90 g (73.5%),
cis/trans 45:55, mp 95–97°C. IR spectrum, ν, cm–1:
3496 (OH), 3240 (NH), 1665 (C–N), 1462 (δCH2,
1
asym.), 1450 (δCH), 1110 (δOH). H NMR spectrum,
δ, ppm: 1.26–1.63 m (26H, CH2), 2.49 t [4H, N(CH2)2,
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 56 No. 6 2020

SADIGOV et al.
1004
J = 7.3 Hz], 2.72 d (1H, CHN, J = 7.2 Hz), 3.46 t (1H,
CHOH, J = 8.2, 7.1 Hz), 3.61 br.s (1H, OH). 13C NMR
spectrum, δC, ppm: 74.3 (C1), 70.9 (C2), 30.2 (C12),
28.7 (C3), 24.6 (C5–C11), 20.4 (C4), piperidin: 54.9
(NCH2), 26.4 (C3′, C5′), 24.7 (C4′). Found, %: C 75.97;
H 12.13; N 5.22. C17H33NO. Calculated, %: C 76.40;
H 12.36; N 5.27.
H 11.12; N 5.21. C16H29NO. Calculated, %: C 76.49;
H 11.55; N 5.58.
6-(Piperidin-1-yl)decahydro-1,4-ethanonaphtha-
len-5-ol (6c) and 3-(piperidin-1-yl)decahydro-1,4-
ethanonaphthalen-2-ol (6′c) (mixture of regioisomers
at a ratio of 92.6:7.4) were synthesized from 6.48 g
(25 mmol) of 4 and 4.25 g (50 mmol) of piperidine.
Yield 5.48 g (83.4%), mp 143–145°C. IR spectrum, ν,
cm–1: 3496 (OH), 3321, 3258 (CN), 2865–2856 (CH2,
sym.), 1528 (CN), 1460 (δCH2, asym.), 1128, 1111
(δOH). 1H NMR spectrum, δ, ppm: 1.30–1.63 m (22H,
CH2), 2.48 t [4H, N(CH2)2, J = 7.2 Hz], 2.69 d [1H,
CHN(CH2)2, J = 9.8, 7.2 Hz], 3.42 d (1H, CHOH, J =
9.8, 7.3 Hz), 3.63 br.s (1H, OH). 13C NMR spectrum,
δC, ppm: 76.5 (C6), 70.8 (C5), 40.2 (C9), 34.8 (C4), 29.8
(C3), 28.8 (C10), 24.7 (C1, C2), 24.5 (C7, C8, C11, C12),
54.8 (NCH2), 26.4 (C3′, C5′), 24.7 (C4′). Found, %:
C 76.93; H 9.94; N 5.0. C17H29NO. Calculated, %:
C 77.57; H 11.03; N 5.32.
2-(Morpholin-4-yl)cyclododecan-1-ol (5d) was
synthesized from 6.57 g (25 mmol) of 3 and 4.35 g
(50 mmol) of morpholine. Yield 4.81 g (71.6%),
cis/trans 45:55, mp 110–113°C. IR spectrum, ν, cm–1:
3494 (OH), 3256 (NH), 3240 (NH), 1525 (C–N),
1460 (δCH2, asym.), 1340, 1125 (C–O–C), 1111, 1082
(δOH). 1H NMR spectrum, δ, ppm: 1.23–1.56 m (20H,
CH2), 2.65 t [4H, N(CH2)2, J = 7.2 Hz], 2.72 d (1H,
CHN, J = 8.0, 7.1 Hz), 3.47 d (1H, CHOH, J = 8.3,
7.3 Hz), 3.56 br.s (1H, OH), 3.62 t [4H, O(CH2)2,
J = 7.3 Hz]. Found, %: C 71.68; H 11.22; N 5.0.
C16H31NO2. Calculated, %: C 71.38; H 11.52; N 5.2.
6-(Morpholin-4-yl)decahydro-1,4-ethanonaph-
thalen-5-ol (6d) and 3-(morpholin-4-yl)decahydro-
1,4-ethanonaphthalen-2-ol (6′d) (mixture of regioiso-
mers at a ratio of 85:15) were synthesized from 6.47 g
(25 mmol) of 4 and 4.35 g (50 mmol) of morpholine.
Yield 5.1 g (77.0%), mp 157–159°C. IR spectrum, ν,
cm–1: 3495 (OH), 3320, 3256 (CN), 1526 (CN), 1462
(δCH2, asym.), 1240, 1123 (C–O–C), 1110, 1082
(δOH). 1H NMR spectrum, δ, ppm: 1.28–1.62 m (16H,
CH2), 2.70 d (1H, CHN(CH2)2, J = 9.8, 7.2 Hz], 2.69 t
[4H, N(CH2)2, J = 7.2 Hz], 3.42 d (1H, CHOH, J =
97.2 Hz), 3.58 br.s (1H, OH), 3.63 t [4H, O(CH2)2, J =
7.2 Hz]. 13C NMR spectrum, δC, ppm: 76.2 (C6), 70.8
(C5), 40.3 (C9), 34.9 (C4), 28.9 (C3, C10), 24.7 (C12),
24.6 (C1, C2, C7, C8, C11), 67.4 (OCH2), 52.5 (NCH2).
Found, %: C 71.92; H 10.06; N 5.12. C16H27NO2.
Calculated, %: C 72.45; H 10.19; N 5.28.
6-(Diethylamino)decahydro-1,4-ethanonaphtha-
len-5-ol (6a) and 3-(diethylamino)decahydro-1,4-
ethanonaphthalen-2-ol (6′a) (mixture of regioisomers
at a ratio of 88:12) were synthesized from 6.48 g
(25 mmol) of 4 and 3.65 g (50 mmol) of diethylamine.
Yield 5.4 g (86.1%), mp 117–119°C. IR spectrum, ν,
cm–1: 3496 (OH), 3321 (NH), 3256 (NH), 2960
(CH3), 2862–2856 (CH2, sym.), 1658 (CN), 1460
1
(δCH2, asym.), 1128, 1110 (δOH). H NMR spectrum,
δ, ppm: 1.05 t (6H, CH3, J = 8.1 Hz), 1.31–1.63 m
(16H, CH2), 2.44 d [4H, N(CH2)2, J = 8.2, 7.0 Hz],
2.68 t (1H, CHN, J = 9.8 Hz), 3.42 d (1H, CHOH, J =
8.2, 7.1 Hz), 3.63 br.s (1H, OH). 13C NMR spectrum,
δC, ppm: 72.3 (C5), 68.7 (C6), 50.7 (C4, C7), 42.4 (C9),
30.7 (C10), 29.5 (C11), 24.7 (C8), 24.5 (C1, C2, C12),
24.3 (C7), 28.7 (C1, C2), 19.5 (C3, C4). Found, %:
C 75.71; H 11.07; N 5.34. C16H29NO. Calculated, %:
C 76.49; H 11.55; N 5.58.
CONFLICT OF INTEREST
The authors declare no conflict of interest.
REFERENCES
6-(Butylamino)decahydro-1,4-ethanonaphtha-
len-5-ol (6b) and 3-(butylamino)decahydro-1,4-
ethanonaphthalen-2-ol (6′b) (mixture of regioisomers
at a ratio of 92.6:7.4) were synthesized from 6.48 g
(25 mmol) of 4 and 3.65 g (50 mmol) of butan-1-
amine. Yield 5.17 g (82.5%), mp 123–126°C. IR spec-
trum, ν, cm–1: 3496 (OH), 3321 (N–H), 3258 (N–H),
2960 (CH3, sym.), 2865–2856 (CH2, sym.), 1528
(δN–H), 1460 (CH2, asym.), 1128, 1111 (δOH).
1H NMR spectrum, δ, ppm: 0.93 t (3H, CH3, J =
8.1 Hz), 1.29–1.68 m (20H, CH2), 2.3 s (1H, NH),
2.57 d (1H, CHNH, J = 9.7, 7.3 Hz), 2.60 d (2H,
NCH2, J = 9.4, 7.3 Hz), 3.43 d (1H, CHOH, J = 9.6,
7.2 Hz), 3.63 br.s (1H, OH). Found, %: C 75.92;
1. Matheu, R., Ertem, M.Z., Grimbert-Surinach, C., Bent-
Buchholz, J., Sala, X., and Llobet, A., ACS Catal., 2017,
vol. 7, p. 6525.
https://doi.org/10.1021/acscatal.7b01860
2. Li, Zh., Gu, J., Qi, Sh., Wu, D., Gao, L., Chen, Z., Guo, J.,
Li, X., Wang, Y., Yang, X., and Tu, Y., J. Am. Chem. Soc.,
2017, vol. 139, p. 14364.
https://doi.org/10.1021/jacs.7b07965
3. Bergmeier, S.C., Tetrahedron, 2000, vol. 56, p. 2561.
https://doi.org/10.1016/S0040-4020(00)00149-6
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 56 No. 6 2020

SYNTHESIS OF AMINO ALCOHOLS
1005
4. Kas’yan, L.I. and Pal’chikov, V.A., Russ. J. Org. Chem.,
2010, vol. 46, p. 1.
pounds. Reactivity), Dnepropetrovsk: Dnepropetr. Nats.
Univ., 2003.
https://doi.org/10.1134/S107042801001001X
14. Alimardanov, Kh.M., Sadygov, O.A., Suleimanova, E.T.,
Dzhafarova, N.A., Abdullaeva, M.Ya., and Babaev, N.R.,
Russ. J. Appl. Chem., 2009, vol. 82, p. 1255.
5. Kuehnel, M.F., Orchard, K.L., Dalle, K.E., and
Reisner, E., J. Am. Chem. Soc., 2017, vol. 139, p. 7217.
https://doi.org/10.1021/jacs.7b00369
https://doi.org/10.1134/S1070427209070180
15. Malinovskii, M.S., Okisi olefinov i ikh proizvodnykh
6. Heinemann, F., Karges, J., and Gasser, G., Acc. Chem.
Res., 2017, vol. 50, p. 2727.
(Olefin Oxides), M.: Goskhimizdat, 1961.
https://doi.org/10.1021/acs.accounts.7b00180
16. Sadygov, O.A., Alimardanov, Kh.M., and Ismailo-
va, Sh.I., Russ. J. Gen. Chem., 2018, vol. 88, p. 862.
https://doi.org/10.1134/S1070363218050031
7. Korotkikh, N.I., Losev, G.A., Lipnitskii, V.F., Kalistra-
tov, S.G., Sokolova, A.S., and Shvaika, O.P., Pharm.
Chem. J., 1993, vol. 25, p. 67.
17. Martınez, A.G., Vilar, E.T., Fraile, A.G., de la Moya
https://doi.org/10.1007/BF00772856
Cerero, S., and Martınez Ruiz, P., Tetrahedron: Asym-
́
metry, 1998, vol. 9, no. 10, p. 1737.
8. de Souza Fernandes, F., Fernandes, T.S., da Sil-
veira, L.G., Caneschi, W., Lourenço, M.C.S, Diniz, C.G.,
de Oliveira, P.F., Martins, S.P.L., Pereira, D.E.,
Tavares, D.C., Le Hyaric, M., de Almeida, M.V., and
Couri, M.R.C., Eur. J. Med. Chem., 2016, vol. 108,
p. 203.
https://doi.org/10.1016/j.ejmech.2015.11.037
9. Pal’chikov, V.A., Russ. J. Org. Chem., 2013, vol. 49,
p. 787.
https://doi.org/10.1016/S0957-4166(98)00132-3
18. Martınez, A.G., Vilar, E.T., Fraile, A.G., de la Moya
́
Cerero, S., Martınez-Ruiz, P., and Villas, P.Ch., Tetra-
́
hedron: Asymmetry, 2002, vol. 13, p. 1.
https://doi.org/10.1016/S0957-4166(02)00011-3
19. Sadygov, O.A., Alimardanov, Kh.M., Ismailova, Sh.I.,
and Babaev, N.R., Russ. J. Gen. Chem., 2018, vol. 88,
p. 650.
https://doi.org/10.1134/S1070428013060018
https://doi.org/10.1134/S1070363218040072
10. Kuliev, A.M., Khimiya i tekhnologiya prisadok k maslam
i toplivam (Chemistry and Technology of Oil and Fuel
Additives), Moscow: Khimiya, 1985.
20. Alimardanov, Kh.M., Sadigov, O.A., Garibov, N.I.,
Dadashova, N.R., Almardanov, M.B., and Kuliev, A.D.,
Pet. Chem., 2017, vol. 57, p. 415.
https://doi.org/10.1134/S0965544117050024
11. Mashkovskii, M.D., Lekarstvennye sredstva (Medicines),
Moscow: Meditsina, 2002, 14th ed.
21. Alimardanov, Kh.M., Sadygov, O.A., Dzhalilova, A.A,
Almardanova, M.B., and Kuliev, A.D., Azerb. Khim. Zh.,
2015, no. 3, p. 67.
22. Colthup, N.B., Daly, L.H., and Wiberley, S.E., Introduc-
tion to Infrared and Raman Spectroscopy, Boston:
Academic, 1990, 3rd ed.
12. Tandon, V.K., Kumar, M., Awasthi, A.K., Saxena, H.O.,
and Goswamy, G.K., Bioorg. Med. Chem. Lett., 2004,
vol. 14, p. 3177.
https://doi.org/10.1016/j.bmcl.2004.04.009
13. Kas’yan, L.I., Kas’yan, A.O., Okovityi, S.I., and
Tarabara, I.N., Alitsiklicheskie epoksidnye soedineniya.
Reaktsionnaya sposobnost’ (Alicyclic Epoxy Com-
23. Derome, A.E., Modern NMR Techniques for Chemistry
Research, Oxford: Pergamon, 1987.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 56 No. 6 2020