Nitrosylsulfuric acid as a tandem reagent in the synthesis of 3,5-diarylisoxazoles from 1,2-diarylcyclopropanes

Article abstract of DOI:10.1007/s11172-019-2540-1

It was demonstrated that nitrosylsulfuric acid can be successfully used as a tandem nitrosating and oxidizing agent in the synthesis of 3,5-diarylisoxazoles from 1,2-diarylcyclopropanes. The reaction proceeds highly regioselectively in the case of symmetr

Full text of DOI:10.1007/s11172-019-2540-1

Russian Chemical Bulletin, International Edition, Vol. 68, No. 6, pp. 1200—1203, June, 2019
1200
Nitrosylsulfuric acid as a tandem reagent in the synthesis
of 3,5-diarylisoxazoles from 1,2-diarylcyclopropanes
O. B. Bondarenko, A. I. Komarov, G. L. Karetnikov, S. N. Nikolaeva, and N. V. Zyk
Department of Chemistry, M. V. Lomonosov Moscow State University,
Build. 3, 1 Leninskie Gory, 119991 Moscow, Russian Federation.
E-mail: k527.5msu@gmail.com
It was demonstrated that nitrosylsulfuric acid can be successfully used as a tandem nitro-
sating and oxidizing agent in the synthesis of 3,5-diarylisoxazoles from 1,2-diarylcyclopropanes.
The reaction proceeds highly regioselectively in the case of symmetric diarylcyclopropanes. The
mixtures of regioisomeric 3,5-diarylisoxazoles were obtained from non-symmetric 1,2-diaryl-
cyclopropanes.
Key words: 3,5-diarylisoxazoles, 1,2-diarylcyclopropanes, nitrosylsulfuric acid, nitrosation,
oxidation.
Representatives of the isoxazole and isoxazoline classes,
connected by a single step of oxidative transformation, are
known for their anti-inflammatory, antifungal, and analgesic
properties. They are also effective against HIV and
Alzheimer´s disease.1,2 According to recent studies, the 3,5-di-
arylisoxazole fragment is a convenient structural unit in the
synthesis of compounds with potential biological activity.
This fragment is found in synthetic analogs of com-
bretastatin А4,3,4 and is used as bioisosteres in drugs applied
to treat and prevent leishmaniasis and Chagas disease.5
Due to their rigid structure, derivatives of 3,5-diphenyl-
isoxazole are used in the design of liquid crystal materials6
and molecular hubs capable of accumulating light energy.7
Among many ways to construct the isoxazole/isox-
azoline cycle, the main ones are [3+2]-dipolar cyclo-
addition of nitrile oxides to multiple bonds8 and the reac-
tion of hydroxylamine with -diketones or their synthetic
equivalents;9,10 the nitrosation reaction of three-mem-
bered carbocycles has been further developed in recent
years.11 It should be noted that the cyclopropane fragment
imparts conformational rigidity to the molecules of
physiologically active compounds and, at the same time,
it can be easily modified using cycloaddition reactions,
the ring-expansion and ring-opening reactions.12 The pos-
sibility of further transformation of three-membered
carbocycles in such structures opens up new prospects. It
is directly related to the search for new reagents, including
nitrosating agents. Earlier, we carried out the nitrosation-
heterocyclization of readily accessible, but hardly reactive,
gem-dihalocyclopropanes using the activation of nitrosyl
chloride with sulfur trioxide. This provided direct access
to 5-haloisoxazoles of various structures.13—15 Continuing
research in this direction, we used nitrosylsulfuric acid
(NSA) as a nitrosating reagent. Note that nitrosylsulfuric
acid is a commercially available nitrosating reagent that
is widely used in technological schemes.16 In the present
work, 1,2-diarylcyclopropanes, available by various meth-
ods, were used as the objects for nitrosation.17,18
It is known that nitrosation of 1,2-diarylcyclopropanes
regardless of the nature of the nitrosating agent (NaNO2/
CF3CO2H,19 NOBF4,20 NOCl•2SO321) results in 3,5-di-
aryl-4,5-dihydroisoxazoles (isoxazolines). At the same
time, an excess of nitrosating reagent (2 equiv. of NaNO2/
CF3CO2H) afforded 3,5-diarylisoxazoles, the dehydroge-
nation (oxidation) products of the corresponding isox-
azolines.22
In this work, we have showed that in the presence of
an excess of nitrosylsulfuric acid, which is able to exhibit
both nitrosating and oxidative properties,23 1,2-diaryl-
cyclopropanes transform readily and smoothly into the
corresponding 3,5-diarylisoxazoles via successive steps of
nitrosation-heterocyclization and oxidation. Earlier, we
reported that NSA is a convenient reagent for the oxidation
of 3,5-diaryl-4,5-dihydroisoxazoles to the corresponding
3,5-diarylisoxazoles.24 Indeed, isoxazoline 2a and the
corresponding isoxazole 3a were obtained by the reaction
of 1,2-diphenylcyclopropane 1a with 1 equiv. of NSA in
dichloromethane at room temperature. The reaction
mixture contained up to 30% of the starting cyclopropane
1a (Scheme 1; Table 1, run 1). Increasing amount of NSA
to 2.0—2.5 equiv. resulted in quantitative conversion of
cyclopropane 1a to isoxazole 2a (see Table 1, run 4). The
search for optimal reaction conditions showed that the
most suitable solvent for the reaction is nitromethane. In
this solvent, the reactions proceeded cleaner and faster
(see Table 1, runs 3 and 4).
In the case of symmetric 1,2-diarylcyclopropanes
1а—с, the reaction proceeded highly regioselectively with
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 6, pp. 1200—1203, June, 2019.
1066-5285/19/6806-1200 © 2019 Springer Science+Business Media, Inc.

Nitrosylsilfuric acid as a tandem reagent
Russ. Chem. Bull., Int. Ed., Vol. 68, No. 6, June, 2019
1201
Table 1. Optimization of the reaction conditions of nitrosation-oxidation of cyclopropane 1a in the presence of nitro-
sylsulfuric acidа
Run
Solvent
NOHSO4 (equiv.)
t/h
Conversion of 1а (%)b
Yield (%)
2а
3а
1
2
3
4
CH2Cl2
CH2Cl2
MeNO2
MeNO2
1.0
1.8
1.3
2.0
20
20
21
20
170
100
100
100
36
63
69
—
10
16
23
90
а Conditions: [С0]1a = 0.1 mol L–1, 20 С.
b Conversion of cyclopropane 1a and the yield of compounds 2a and 3a were evaluated by 1H NMR spectroscopy.
as a characteristic one for isoxazoles 5a—d.25 Afterwards,
the isomers were assigned using the NMR spectra. The
predominant formation of one or another regioisomer
during the reaction is obviously related to the stability of
the intermediate carbocation (A or B) and is determined
by the nature and position of the substituents in the aro-
matic rings.
Scheme 1
Scheme 3
the cleavage of the С(1)—С(2) bond of the cyclopropane
ring to give good yields of the corresponding 3,5-diaryl-
isoxazoles 3а—с (Scheme 2).
Scheme 2
Compounds
4—6
a
b
c
d
Ar
Ratio
5 : 6
1 : 4.5
1 : 1.8
1 : 1.5
1.4 : 1
Yield of
5 + 6 (%)
45
3,4-Me2C6H3
2,5-Me2C6H3
4-BrC6H4
64
98
73
2-FC6H4
Reagents and conditions: NOHSO4 (2.5 equiv.), MeNO2, 20 C.
Compounds 1 and 3
R
H
F
Yield of 3 (%)
Thus, in present work was demonstrated that nitrosyl-
sulfuric acid can be successfully used for the synthesis of
3,5-diarylisoxazoles from 1,2-diarylcyclopropanes. The
advantages of this method are the simplicity of the syn-
thesis and the availability of the starting compounds,
namely, 1,2-diarylcyclopropanes and nitrosylsulfuric acid.
a
b
с
65
78
84
Br
Reagents and conditions: NOHSO4 (2.5 equiv.), MeNO2, 20 C.
In the case of asymmetric 1,2-diarylcyclopropanes
4a—d, selective cleavage of the С(1)—С(2) bond of the
cyclopropane occurred. However, the reaction produced
the mixtures of regioisomeric 3,5-diarylisoxazoles 5 and
6 (Scheme 3). The location of aryl substituents in the
isoxazole cycle was determined by the mass spectrometry
using an ion with m/z 105 corresponding to the [PhC=O]+
Experimental
1Н, 13С, and 19F spectra of compounds were recorded in
CDCl3 using Bruker Avance-400 and Agilent 400-MR spectrom-
eters with working frequencies of 400.13, 100.67, and 376.29

1202
Russ. Chem. Bull., Int. Ed., Vol. 68, No. 6, June, 2019
Bondarenko et al.
1
MHz, respectively (internal standards were HMDS for Н and
13С, and CFCl3 for 19F). Chemical shifts were measured with an
accuracy of 0.01 ppm, spin-spin coupling constants were mea-
sured with an accuracy of 0.1 Hz. Mass spectra were recorded
using a Thermo Scientific TSQ 8000 gas chromatograph-
mass spectrometer (capillary chromatographic column SPBTM-5
(15 m0.25 mm), carrier gas was helium, gas flow rate was
1 mL min–1). The ionization method was electron impact (elec-
tron energy was 70 eV). Temperature conditions were 70 С
(2 min), heating at a rate of 20 С min–1, maintaining at 280 С
(5 min). The melting points of the obtained compounds were
measured using a Mel-TempII instrument and were not cor-
rected. The course of the reactions and the purity of the products
were monitored by TLC on Silufol plates. The starting 1,2-diaryl-
cyclopropanes 1a and 4c were obtained by a known method.17
trans-1,2-Bis(4-bromophenyl)cyclopropane (1c) was obtained
by bromination of trans-1,2-diphenylcyclopropane.26 The start-
ing cyclopropanes, with the exception of compound 1c, were
introduced into the reaction as a mixtures of cis/trans isomers in
a 1 : 1 ratio. Nitrosylsulfuric acid was obtained according to
a known method27 and stored at –20 C under a layer of dichloro-
methane in a tightly closed flask. Nitrosylsulfuric acid was
transferred to a weighted round-bottom flask before the reaction
and dichloromethane was evaporated using a rotary evaporator.
Dry solid reagent was quickly weighed to carry out the reaction.
Nitrosation of 1,2-diarylcyclopropanes 1а—с and 4a—d (gen-
eral procedure). Cyclopropane (1 mmol), nitromethane (10 mL),
and NSA (0.176 g, 1.5 mmol) were loaded into a 50-mL round-
bottom flask equipped with a magnetic stirrer. The reaction
mixture was stirred at room temperature for 1.0—1.5 h, then
additional amount of NSA (0.117 g, 1 mmol) was added and
stirring was continued until completion of the reaction (TLC
monitoring). Then the mixture was neutralized with a 0.1 M
solution of NaHCO3 and the organic compounds were extracted
with chloroform (320 mL). The organic extracts were combined,
dried over sodium sulfate, and the solvent was evaporated using
a rotary evaporator. Isoxazoles 3а—с were purified by recrystal-
lization from ethanol. Isoxazoles 6а,b were isolated in a pure
form by fractional crystallization (diethyl ether—hexane), obtain-
ing up to 35% of the pure isomer. The other compounds
were isolated by preparative column chromatography (silica gel
40/100, eluent was benzene—petroleum ether, 3 : 2).
7.25 (d, 1 Н, Ar, 3J = 7.2 Hz); 7.49—7.51 (m, 3 Н, Ar); 7.60
(d, 1 Н, Ar, 3J = 7.2 Hz); 7.68 (s, 1 Н, Ar); 7.84—7.86 (m, 2 Н, Ar).
13С NMR, : 19.73 and 19.76 (2 СН3), 97.4 (С(4)is), 124.2 (СН),
125.1 (СН), 125.8 (2 CHPh), 126.6 (С), 127.6 (С), 128.9
(2 CHPh), 130.08 (СН), 130.11 (СН), 137.2 (C—Me), 138.8
(C—Me), 163.0 (C=N or C—O), 170.1 (C—O or C=N). MS,
m/z (Irel (%)): 249 (15) [M]+, 172 (10) [M – Ph]+, 105 (100)
[PhCO]+, 77 (18) [Ph]+, 51 (33), 39 (20).
5-(3,4-Dimethylphenyl)-3-phenylisoxazole (6a). M.p.
124—126 С. 1Н NMR, : 2.33 (s, 3 Н, CH3); 2.35 (s, 3 Н, CH3);
6.78 (s, 1 H, C(4)His); 7.25 (d, 1 Н, Ar, 3J = 7.3 Hz); 7.47—7.49
3
(m, 3 Н, Ar); 7.58 (d, 1 Н, Ar, J = 7.3 Hz); 7.63 (s, 1 Н, Ar);
7.86—7.89 (m, 2 Н, Ar). 13С NMR, : 19.79 and 19.80 (СН3),
96.8 (С(4)is), 123.3 (СН), 126.8 (2 CHPh), 126.9 (СН), 127.9
(С), 128.9 (2 CHPh), 129.3 (С), 129.9 (СН), 130.2 (СН), 137.3
(C—Me), 139.2 (C—Me), 162.9 (C=N or C—O), 170.7 (C—O
or C=N). MS, m/z (Irel (%)): 249 (23) [M]+, 133 (100) [ArCO]+,
105 (41) [Ar]+, 103 (18) [C6H3CO]+, 77 (70) [Ph]+, 51 (45),
39 (22).
3-(2,5-Dimethylphenyl)-5-phenylisoxazole (5b) and 5-(2,5-di-
methylphenyl)-3-phenylisoxazole (6b) were synthesized from
cyclopropane 4b (0.7 g) as a mixture in 64% yield. Found (for
mixture of 5b and 6b) (%): С, 81.62; H, 6.00; N, 5.55. C17H15NO.
Calculated (%): C, 81.90; H, 6.06; N, 5.62.
3-(2,5-Dimethylphenyl)-5-phenylisoxazole (5b).* 1Н NMR,
: 2.39 (s, 3 Н, СН3); 2.49 (s, 3 Н, СН3); 6.70 (s, 1 Н, C(4)His);
7.19 (m, 2 Н, Ar); 7.40 (s, 1 Н, Ar); 7.49—7.52 (m, 3 Н, Ph);
7.85—7.87 (m, 2 Н, Ph). 13С NMR, : 20.6 (CH3), 20.9 (CH3),
100.2 (С(4)is) 125.9 (2 CHPh), 127.6 (C), 128.6 (С), 129.0
(2 CHPh), 130.1 (СН), 130.2 (СН), 130.3 (СН), 131.1 (СН),
133.7 (C—Me), 135.5 (C—Me), 163.8 (C=N or C—O), 169.5
(C—O or C=N). MS, m/z (Irel (%)): 249 (25) [M]+, 248 (24)
[M – 1]+, 172 (23) [M – Ph]+, 144 (25) [M – PhCO]+, 105 (59)
[PhCO]+, 77 (100) [Ph]+, 51 (50).
5-(2,5-Dimethylphenyl)-3-phenylisoxazole (6b). M.p. 63 С.
1Н NMR, : 2.40 (s, 3 Н, СН3); 2.53 (s, 3 Н, СН3); 6.72 (s, 1 Н,
C(4)His); 7.18 (d, 1 Н, Ar, 3J = 7.8 Hz); 7.22 (d, 1 Н, Ar,
3J = 7.8 Hz); 7.48—7.52 (m, 3 Н, Ph); 7.60 (s, 1 Н, Ar);
7.90—7.91 (m, 2 Н, Ph). 13С NMR, : 20.5 (CH3), 20.6 (CH3),
100.1 (С(4)is), 126.3 (С), 126.4 (2 CHPh), 128.5 (2 CHPh), 128.6
(CH), 128.9 (C), 129.5 (CH), 130.4 (CH), 130.9 (CH), 132.7
(C—Me), 135.4 (C—Me), 162.2 (C=N or C—O), 170.3 (C—O
or C=N). MS, m/z (Irel (%)): 249 (35) [M]+, 146 (25), 133 (35)
[ArCO]+, 105 (35) [Ar]+, 103 [C6H3CO]+, 77 (100) [Ph]+,
63 (25), 51 (65), 39 (30).
3,5-Diphenylisoxazole (3а). Yield 65%, Rf 0.7, m.p. 140 С
(cf. Ref. 11: m.p. 140—142 С). 1Н NMR, : 6.86 (s, 1 Н, C(4)His);
7.51—7.54 (m, 6 Н, Ar); 7.89—7.91 (m, 4 Н, Ar).
3,5-Bis(4-fluorophenyl)isoxazole (3b). Yield 78%, m.p. 188 С
3-(4-Bromophenyl)-5-phenylisoxazole (5c) and 5-(4-bromo-
phenyl)-3-phenylisoxazole (6c) were obtained from cyclopropane
4c (0.40 g) as a mixture in 98% yield.
1
(cf. Ref. 24: m.p. 190 С). Н NMR, : 6.76 (s, 1 H, C(4)His);
7.20 (m, 4 H, Ar); 7.86 (m, 4 H, Ar).
3,5-Bis(4-bromophenyl)isoxazole (3с). Yield 84%, m.p.
218 С (cf. Ref. 28: m.p. 214 С). 1Н NMR, : 6.83 (s, 1 Н, C(4)His);
7.65 (m, 4 Н, Ar); 7.74 (m, 4 Н, Ar).
3-(4-Bromophenyl)-5-phenylisoxazole (5c). M.p. 184 С
(cf. Ref. 11: m.p. 182—183 С). 1Н NMR, : 6.83 (s, 1 Н,
C(4)His); 7.52 (m, 3 Н, Ar); 7.65 (d, 2 Н, Ar, 3J = 8.4 Hz); 7.77
(d, 2 Н, Ar, 3J = 8.4 Hz); 7.86 (m, 2 Н, Ar). 13С, : 97.3 (С(4)is),
124.3 (CBr), 125.9 (2 СН), 127.3 (C), 128.1 (C), 128.3 (2 СН),
129.1 (2 СН), 130.4 (СН), 132.2 (2 СН), 162.1 (C=N or C—O),
170.8 (C—O or C=N). MS, m/z (Irel (%)): cluster 301 (10),
299 (9) [M]+; cluster 157 (4), 155 (4) [C6H4Br]+; 115 (6) [M – Br –
– PhCO]+, 105 (100) [PhCO]+, 77 (65) [Ph]+, 51 (29).
5-(4-Bromophenyl)-3-phenylisoxazole (6c). M.p. 164 С
(cf. Ref. 29: m.p. 156—158 С). 1Н NMR, : 6.86 (s, 1 Н, C(4)His);
3-(3,4-Dimethylphenyl)-5-phenylisoxazole (5a) and 5-(3,4-di-
methylphenyl)-3-phenylisoxazole (6a) were synthesized from
cyclopropane 4а (0.96 g) as a mixture in 45% yield. Found (for
mixture of 5a and 6a) (%): С, 81.97; H, 6.05; N, 5.57. С17Н15NO.
Calculated (%): C, 81.90; H, 6.06; N, 5.62.
3-(3,4-Dimethylphenyl)-5-phenylisoxazole (5a).* 1Н NMR,
: 2.29 (s, 3 Н, CH3); 2.32 (s, 3 Н, CH3); 6.82 (s, 1 H, C(4)His);
3
* Isoxazoles 5a and 5b are characterized from the mixtures
5a : 6a and 5b : 6b = 2 : 1.
7.50 (m, 3 H, Ar); 7.66 (d, 2 H, Ar, J = 8.7 Hz); 7.74 (d, 2 H,
Ar, 3J = 8.7 Hz); 7.88 (m, 2 H, Ar). 13С NMR, : 97.9 (С(4)is),

Nitrosylsilfuric acid as a tandem reagent
Russ. Chem. Bull., Int. Ed., Vol. 68, No. 6, June, 2019
1203
124.6 (CBr), 126.3 (С), 126.8 (2 СН), 127.3 (2 СН), 128.9 (C),
129.0 (2 СН), 130.1 (СН), 132.3 (2 СН), 163.1 (C=N or C—O),
169.3 (CO or C=N). MS, m/z (Irel (%)): cluster 301 (21), 299
(20) [M]+; 220 (2) [M – Br]+, cluster 185 (100), 183 (82)
[BrC6H4C=O]+; cluster 157 (41) 155 (40) [C6H4Br]+, 144 (15)
[M – C6H4Br]+, 89 (25), 77 (42) [Ph]+, 39 (14).
6. A. A. Vieira, F. R. Bryk, G. Conte, A. J. Bortoluzzi,
H. Gallardo, Tetrahedron Lett., 2009, 50, 905.
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24, 1045.
10. S. Tang, J. He, Y. Sun, L. He, X. She, Org. Lett., 2009,
11, 3982.
3-(2-Fluorophenyl)-5-phenylisoxazole (5d) and 5-(2-fluoro-
phenyl)-3-phenylisoxazole (6d) were synthesized from cyclo-
propane 4d (0.20 g) as a mixture in 73% yield. Found (for mixture
5d and 6d) (%): С, 75.15; H, 4.42; N, 5.66. C15H10FNO.
Calculated (%): C, 75.30; H, 4.21; N, 5.85.
11. O. B. Bondarenko, A. Yu. Gavrilova, D. S. Murodov, N. V.
Zyk, N. S. Zefirov, Mendeleev Commun., 2011, 21, 188.
12. I. A. Novakov, A. S. Babushkin, A. S. Yablokov, M. B.
Nawrozkij, O. V. Vostrikova, D. S. Shejkin, A. S. Mkrtchyan,
K. V. Balakin, Russ. Chem. Bull., 2018, 67, 395.
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Chizhov, N. S. Zefirov, Russ. Chem. Bull., 2011, 60, 328.
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Nikolaeva, A. Yu. Gavrilova, N. V. Zyk, Tetrahedron Lett.,
2015, 56, 6577.
15. O. B. Bondarenko, A. A. Vinogradov, A. I. Komarov, A. S.
Smirnov, N. V. Zyk, J. Fluorine Chem., 2016, 185, 201.
16. G. A. Olah, G. K. S. Prakash, Q. Wang, X.-Y. Li, in e-EROS
Encyclopedia of Reagents for Organic Synthesis, John Wiley &
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17. N. М. Kizhner, Zh. Ross. Fiz.-Khim. O-va [J. Russ. Phys-
Chem. Soc.], 1913, 45, 944 (in Russian).
3-(2-Fluorophenyl)-5-phenylisoxazole (5d). M.p. 84 С.
5
1Н NMR, : 7.00 (d, 1 Н, C(4)His, JHF = 3.5 Hz); 7.22 (ddd,
1 Н, Ar, 3J = 7.6 Hz, 4J = 1.1 Hz, 3JHF = 11.1 Hz); 7.28 (td, 1 Н,
Ar, 3JHH = 4JHF = 7.6 Hz, 4JHH = 1.1 Hz); 7.43—7.53 (m, 4 H,
Ph + Ar); 7.87 (m, 2 Н, Ph); 8.06 (td, 1 Н, Ar, 3J = 7.5 Hz,
4J = 1.7 Hz). 13С NMR, : 100.0 (d, C(4)His, JCF = 9.2 Hz);
4
116.4 (d, C(3)HAr, , =
2JCF = 21.7 Hz); 117.2 (d, C(1)Ar 2JCF
= 12.4 Hz); 124.6 (d, CHAr, JCF = 3.5 Hz); 125.8 (2 CHPh);
127.4 (C(1)Ph); 128.9 (2 CHPh); 129.1 (d, CHAr, JCF = 3.1 Hz);
130.2 (CHPh); 131.6 (d, CHAr, JCF = 8.5 Hz); 158.3 (C=N);
1
160.3 (d, С—F, JCF = 251.9 Hz); 170.3 (C—O). 19F NMR, :
–114.3 (m, 1 F). MS, m/z (Irel (%)): 239 (16) [M]+, 162 (6)
[M – Ph]+, 134 (5) [M – PhCO]+, 105 (100) [PhCO]+, 77
(63) [Ph]+.
5-(2-Fluorophenyl)-3-phenylisoxazole (6d). M.p. 91—92 С
(cf. Ref. 24: m.p. 91—92 С). 1Н NMR, : 7.05 (d, 1 Н, С(4)Нis,
5JHF = 3.7 Hz); 7.23 (ddd, 1 Н, Ar, 3JHF = 10.9 Hz, J = 7.8 Hz,
J = 1.0 Hz); 7.31 (td, 1 H, Ar, J = 7.8 Hz, J = 1.0 Hz); 7.42—7.47
(m, 1 Н, Ar); 7.48—7.50 (m, 3 H, Ar); 7.91 (m, 2 Н, Ar); 8.03
(td, 1 Н, Ar, J = 7.8 Hz, J = 1.7 Hz).
18. H. Tomioka, Y. Ozaki, Y. Koyabu, Y. Izawa, Tetrahedron
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Univ., Ser. Khim. [Moscow Univ. Chem. Bull.], 1994, 35, 186
(in Russian).
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The authors are grateful to Thermo Fisher Scientific,
Inc., MS Analytics (Moscow), and personally to Professor
A. A. Makarov (Thermo Fisher Scientific, Inc.) for provid-
ing the mass spectrometric equipment used in this work.
The authors are also grateful to L. G. Saginova (M. V.
Lomonosov Moscow State University) for kindly provid-
ing some of 1,2-diarylcyclopropanes used in this study.
The work was financially supported by the Russian
Foundation for Basic Research (Project Nos 15-03-04260
and 18-33-01109).
25. L. G. Saginova, I. L. Kukhareva, А. Т. Lebedev, Yu. S.
Shabarov, Zh. Org. Khim. [Russ. J. Org. Chem.], 1991, 27,
1852 (in Russian).
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Received January 28, 2019;
in revised form March 4, 2019;
accepted March 20, 2019