Study of the Features of the Reaction of Arylcyclopropanes with Nitrozonium Ethyl Sulfate or Nitrozonium Tetrafluoroborate

Article abstract of DOI:10.1134/S107042802005005X

Abstract: The reactions of diaryl-, aryl-, and alkyl–arylcyclopropanes with ethyl nitrite in the presence of sulfur trioxide and sulfur trioxide dioxane complex, as well as the reactions of 1-alkyl-2-arylcyclopropanes with NOBF₄ were studied. It was found that the attack of the nitrosonium cation, accompanied by the formation of a benzyl carbocation, leads to the formation of isoxazolines. The introduction of bulky alkyl substituents into the cyclopropane ring changes the regioselectivity of nitrosation, favoring the attack of the electrophilic particle on the benzyl position and leading to the competitive formation of an alkyl carbocation. Depending on the structure of the alkyl substituent, both products of intramolecular heterocyclization accompanied by skeletal rearrangements and products formed with the participation of an external nucleophile are formed.

Full text of DOI:10.1134/S107042802005005X

ISSN 1070-4280, Russian Journal of Organic Chemistry, 2020, Vol. 56, No. 5, pp. 753–762. © Pleiades Publishing, Ltd., 2020.
Russian Text © The Author(s), 2020, published in Zhurnal Organicheskoi Khimii, 2020, Vol. 56, No. 5, pp. 693–704.
Study of the Features of the Reaction of Arylcyclopropanes
with Nitrozonium Ethyl Sulfate or Nitrozonium
Tetrafluoroborate
A. Yu. Gavrilovaa,*, O. B. Bondarenkoa, V. N. Tikhanushkinaa,
T. A. Solodovnikovaa, and N. V. Zyka
a Lomonosov Moscow State University, Moscow, 119991 Russia
*e-mail: augava@gmail.com
Received December 25, 2019; revised February 12, 2020; accepted February 19, 2020
Abstract—The reactions of diaryl-, aryl-, and alkyl–arylcyclopropanes with ethyl nitrite in the presence of sulfur
trioxide and sulfur trioxide dioxane complex, as well as the reactions of 1-alkyl-2-arylcyclopropanes with NOBF4
were studied. It was found that the attack of the nitrosonium cation, accompanied by the formation of a benzyl
carbocation, leads to the formation of isoxazolines. The introduction of bulky alkyl substituents into the cyclopro-
pane ring changes the regioselectivity of nitrosation, favoring the attack of the electrophilic particle on the benzyl
position and leading to the competitive formation of an alkyl carbocation. Depending on the structure of the alkyl
substituent, both products of intramolecular heterocyclization accompanied by skeletal rearrangements and products
formed with the participation of an external nucleophile are formed.
Keywords: arylcyclopropane, nitrosation, alkyl nitrite, nitrosonium tetrafluoroborate, isoxazoline, regioselectivity,
skeletal rearrangements
DOI: 10.1134/S107042802005005X
The reaction of alkenes with nitrosating reagents
opens the way to the synthesis of a wide range of pro-
ducts: nitroso and nitro compounds, oximes, ketones,
and amines [1]. Nitrosonium ethyl sulfate (EtOSO2ONO)
is a convenient nitrosating reagent, which has an ionic
structure and is obtained in situ by the reaction of ethyl
nitrite with sulfur trioxide. This reagent was used to pre-
pare keto sulfates in high yields [2], but has never been
studied in reactions with cyclopropanes, even though such
reactions might be expected to provide both isoxazolines
(a direction characteristic of nitrosation of cyclopropanes
[3–11]) and 1,3-keto sulfates (with a double excess of the
reagent) (Scheme 1) [2].
nitrosonium tetrafluoroborate. It was found that the nitro-
sation of 1,2-diarylcyclopropanes 1a–1d and 1-methyl-
1-phenylcyclopropane 3 with ethyl nitrite in the presence
of both free sulfur trioxide and sulfur trioxide dioxane
complex (used as a mild source of sulfur trioxide), leads,
irrespective of the reagent–cyclopropane ratio, to the ex-
clusive formation of isoxazolines 2 and 4 in high yields
(Scheme 2), which is consistent with the reported results
of Misuno et al. for NOBF4 [3].
The nitrosation of phenylcyclopropane with nitro-
sonium tetrafluoroborate leads exclusively to isoxaline
6a. The reactions of monoarylcyclopropanes 5a and
5b with ethyl nitrite in the presence of SO3 give, along
with isoxalines 6a and 6b, minor amounts of aldehydes
7a and 7b (Scheme 3).
The aim of the present work was to study the be-
havior of nitrosonium ethyl sulfate in reactions with
cyclopropanes and compare its reactivity with that of
Scheme 1.
EtOSO2ONO
EtOSO2ONO
O
OSO2OEt
N
O
753

754
GAVRILOVA et al.
Scheme 2.
a or b
Ar'
Ar
Ar
Ar'
N
O
1a–1d
2a–2d (71–100%)
Ph
a
Ph
H3C
CH3
O N
3
4 (94%)
Ar = Ar' = 4-MeOC6H4 (a), Ph (b), 4-FC6H4 (c), Ar = 4-MeOC6H4, Ar' = Ph (d).
Reagents and conditions: a, EtONO (2 equiv), SO3 (1 equiv), CH2Cl2, –55÷20°C, 2 h;
b, EtONO (2 equiv), dioxane·SO3 (1 equiv), CH2Cl2, –55÷20°C, 2 h.
We suggest that aldehydes are formed by the isoxaline
at reduced temperatures would favor higher yields of
compounds 6a and 6b. Actually, the optimal conditions
for reacting monoarylcyclopropanes with ethyl nitrite in
the presence of SO3 were found to be as follows: first,
an equimolar reagent ratio and, second, hydrolysis of the
reaction mixture at a temperature not higher than –10°C.
Failure to comply with the second condition leads to
the formation of a complex mixture of products and a
significant tarring of the reaction mixture.
ring opening under the action of ethyl hydrogen sulfate
released during reaction. In the presence of sulfur tri-
oxide dioxane complex, only traces of aldehydes formed,
because the proton was bound by dioxane.
To check the validity of this suggestion, we treated
with concentrated sulfuric acid the reaction mixtures
obtained after the nitrosation of cyclopropanes 5a and
5b. The mixture of isoxaline 6b and aldehyde 7b, result-
ing from the nitrosation of methoxyphenyl derivative 5b,
contained initially 9% of the aldehyde, while treatment
with H2SO4 increased the fraction of the aldehyde to
67%. With phenyl derivative 5a, the changes were not so
essential: the fraction of the aldehyde in the mixture of
isoxaline 6a and aldehyde 7a before and after treatment
was 9 and 17%, respectively. It was thus concluded that
treatment of the reaction mixture with saturated NaHCO3
Further on we studied the synthetic potential of the
nitrosation of 1-alkyl-2-arylcyclopropanes. With these
substrates, there are three possible results of the attack
on the cyclopropane ring: ring opening by the more reac-
tive C1–C2 bond (routes A and B) and by the C2–C3 bond
(route C) (Scheme 4). Routes A and C are more favorable
for electronic reasons, because they involve formation
of a benzyl carbocation, which, as follows from the re-
Scheme 3.
H3O+
O
a–c
Ar
+
Ar
5a, 5b
O
N
Ar
6a, 94% (a)
59% (b)
7a, 0% (a)
19% (b)
33% (c)
4% (c)
6b, 57% (b)
91% (c)
7b, 10% (b)
2% (c)
Ar = Ph (a), 4-MeOC6H4 (b).
Reagents ans conditions: a, NOBF4 (1 equiv), CH3NO2, 20°C; b, EtONO (2 equiv), SO3 (1 equiv),
CH2Cl2, –55÷20°C, 2 h; c, EtONO (2 equiv), dioxane·SO3 (1 equiv), CH2Cl2, –55÷0°C, 2 h.
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STUDY OF THE FEATURES OF THE REACTION OF ARYLCYCLOPROPANES
755
Scheme 4.
R
C
Ar
R
Ar
N O
O
N
R
Ar
Products of the opening of a small
cycle formed without
the participation of oxygen
of the nitroso group
R
Ar
R
Ar
A
B
N
O
O=N
sults obtained with diaryl- and monoarylcyclopropanes,
stabilizes due to nucleophilic assistance of the nitroso
oxygen atom.
12a with nitrosonium tetrafluroborate in acetonitrile
forms ketone 18 with the participation of the solvent as
an external nucleophile. The formation of the keto group
in compounds 16 and 18 and nitroimines 17 is a result of
repeated nitrosation of the initially formed oxime [12–17].
Actually, the reaction with 1-methyl-2-phenylcyclo-
propane 8 forms mainly isoxaline 9 and less isoxaline
10. At the same time, sometimes a little of isoxaline
11 was isolated (Scheme 5). It should be noted that no
reaction products formed with the participation of an
external nucleophile were detected both in the reaction
with nitrosonium ethyl sulfate and in the reaction with
nitrosonium tetrafluoroborate in acetonitrile.
Thus, in this case, the nitrosonium cation prefers to
attack the benzyl position, and the reaction preferentially
occurs by route B (Scheme 4). The different regioselectiv-
ity of nitrosation in this case is obviously explained by
steric reasons. The secondary carbocation formed under
conditions b, c, and d (Scheme 6) is stabilized due to the
involvement of an external nucleophile (ethyl sulfate
anion or acetonitrile) rather than due to intramolecular
heterocyclization.
A radically different regioselectivity takes place with
1-aryl-2-cyclohexylcyclopropanes 12a and 12b. The
reaction of cyclopropane 12a with nitrosonium tetra-
fluoroborate in nitromethane gave more than two times
more isoxaline 15a than isoxalines 13a and 14a together
(Scheme 6). The reaction of cyclopropanes 12a and 12b
with ethyl nitrite in the presence of sulfur trioxide (or
sulfur trioxide dioxane complex) results in preferential
formation of ketones 16b and 16c and nitroimines 17b
and 17c. At the same time, the reaction of cyclopropane
In view of the resulting data, we suggested that ste-
rically hinded cyclopropanes 19 and 20 (Scheme 7)
would, too, occur via the preferential attack of the
electrophilic particle on the benzyl position (route B,
Scheme 3).Actually, the attack of the nitrosonium cation
on the benzyl position contributes much in the case of
1-isopropyl-2-phenylcyclopropane (19) (products 23–30)
Scheme 5.
Me
a–d
Ph
Me
Ph
Me
Ph
+
+
Ph
Me
O N
N O
O N
8
9, 43% (a)
74% (b)
83% (c)
90% (d)
10, 26% (a)
18% (b)
11, 7% (a)
Reagents and conditions: a, NOBF4 (1 equiv), CH3NO2, 20°C; b, EtONO (3 equiv), SO3 (2 equiv),
CH2Cl2, –55÷–20°C, 2 h; c, EtONO (3 equiv), dioxane·SO3 (2 equiv), CH2Cl2, –55÷0°C, 2 h;
d, NOBF4 (2 equiv), CH3CN, 0–20°C.
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756
GAVRILOVA et al.
Scheme 6.
a
Cy
Ph
Cy
Ph
Ph
+
+
N O
O N
O N
13a, 8%
14a, 10%
15a, 34%
13a, 14% (b)
4% (c)
13b , 11% (b)
+
+
14a, 5% (b) + 15a, 9% (b)
6% (c) 2% (c)
14b , 13% (b) + 15b, 8% (b)
b or c
Ar
Cy
12a, 12b
Cy
Ar
Ar
+
Cy
+
N
OSO2OEt
OSO2OEt
O
O2N
16a, 35% (b)
9% (c)
16b, 35% (b)
17a, 20% (b)
4% (c)
17b, 25% (b)
Cy
Ph
d
13a, 5%
+
14a, 5%
+
15a, 0.3% +
O
NHAc
18, 57%
Ar = Ph (a), 4-I-C6H4 (b).
Reagents and conditions: a, NOBF4 (1 equiv), CH3NO2, 20°C; b, EtONO (3 equiv), SO3 (2 equiv),
CH2Cl2, –55÷–20°C, 2 h; c, EtONO (3 equiv), dioxane·SO3 (2 equiv), CH2Cl2, –55÷0°C, 2 h;
d, NOBF4 (2 equiv), CH3CN, 0–20°C.
and becomes the main reaction direction in the case of
1-tert-butyl-2-phenylcyclopropane 20 (products 32–36)
(Scheme 7). However, isoxaline 23, as well as products
28–30 and 36 formed with the participation of an external
nucleophile were isolated in trace amounts. The alkyl car-
bocation formed by the attack of the electrophilic particle
on the benzyl position is mainly stabilized by intramo-
lecular alkylation of the aromatic ring (compounds 26,
27, and 35) and heterocyclization involving the oxygen
or nitrogen atoms of the nitroso group (compounds 24,
32, and 34).
this takes place, the trans-isomers are isolated unchanged
from the reaction mixtures.
The structure of the synthesized compounds was es-
tablished by IR and NMR spectroscopy. The H2C proton
1
signals in the H NMR spectra of compounds 16, 17,
28, 29, and 36 appear as doublet of doublets with large
geminal coupling constants of 16–18 Hz and vicinal
coupling constants spanning the range 3.0–8.5 Hz. The
HCO protons have two common coupling constants
with the CH2 protons and one, small coupling constant
with the cyclohexane H1 proton (compounds 16 and
17) or the H4 proton (compounds 28 and 29). The keto
sulfate HCO proton signals are observed at 5.2 ppm,
while the nitrilimines proton signals are shifted down-
field to 4.7–4.8 ppm. The IR spectrum of compound 28
contains a characteristic carbonyl absorption band at
1690 cm–1. The 13C NMR spectrum displays the C=O car-
bon signal at 196.1 ppm. By contrast, the IR and 13C NMR
spectra of nitrilimine 29 show no signals corresponding
to the carbonyl group. At the same time, the IR spectrum
contains a strong absorption band of the nitro group at
1570 cm–1, while the 13C NMR spectrum contains a signal
Note that during the reaction of cyclopropanes 19 and
20 along route B cyclization was generally preceded by
proton or methyl migration to form carbocations 37 and
38, respectively (Scheme 8). The formation of hydroxy
ketones 25 and 33 can be explained by hydration of the
double bond in oxime 39 at the stage of hydrolysis of the
reaction mixture.
It should be noted that the ethyl nitrite–sulfur trioxide
dioxane complex system is less reactive than the ethyl
nitrite–sulfur trioxide system, which results in incomplete
conversion of the starting cyclopropanes 12a and 19. As
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STUDY OF THE FEATURES OF THE REACTION OF ARYLCYCLOPROPANES
757
Scheme 7.
b or c
b or c
Reagents and conditions: a, NOBF4 (1 equiv), CH3NO2, 20°C; b, EtONO (3 equiv), SO3 (2 equiv),
CH2Cl2, –55÷–20°C, 2 h; c, EtONO (3 equiv), dioxane·SO3 (2 equiv), CH2Cl2, –55÷0°C, 2 h;
d, NOBF4 (2 equiv), CH3CN, 0–20°C.
at 165.5 ppm, which suggests the presence of a C=N–NO2
group. We failed to separate compounds 16a, 17a and
16b, 17b by column chromatography. However, the IR
spectra of the mixtures showed absorption bands both of
the keto and nitro groups.
the region of 6.5 ppm. The IR spectra of compounds 18
and 35 display absorption bands characteristic of amides
at 3270 (NH), 1650 (C=O), and 1560 cm–1 (NH), as well
as the absorption band of the keto group at 1690 cm–1
(C=O). The 13C NMR signal of the carbonyl group linked
to the aromatic ring is observed at 199 ppm, and that of
the acetamide carbonyl group appears at 169 ppm.
The sets of signals and coupling constants in the 1H
NMR spectra of compounds 18 and 35 are similar to
those in the above-described spectra of keto sulfates,
but the HCN proton signal is observed at 4.13 ppm, and
a characteristic acetamide HN proton signal appears in
Thus, the nitrosation of 1-methyl-2-phenylcyclopro-
pane and diaryl- and monoarylcyclopropanes with nitro-
sonium ethyl sulfate and nitrosonium tetrafluoroborate
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758
GAVRILOVA et al.
Scheme 8.
19 or 20
NO+
Me
Me
Ph
Me
R
[1,2]CH3
Ph
26
27, 32, 34, 35
R
R = H, CH3
N
O
N
O
Me
38
[1,2]H
R = H
–H+
Ph
H
Ph
Me
R
H3O+
24
25, 23
N
N
Me
O
Me
HO
Me
37
39
results in preferential formation of isoxalines and is a
convenient method of synthesis of such heterocycles.
Irrespective of the reagent, the nitrosation of 1-alkyl-
2-arylcyclopropanes with bulky substituents leads to
mixtures of isomeric isoxalines and cyclopropane ring
opening products formed without the involvement of the
oxygen atom of the nitroso group, which decreases the
preparative significance of this reaction.
solution of ethyl nitrite in anhydrous methylene chloride
was slowly added dropwise with stirring under dry argon
at –50 to –40°C to a solution of sulfur trioxide or sulfur
trioxide dioxane complex in anhydrous methylene chlo-
ride. The reaction mixture was stirred at this temperature
for 30 min, after which a solution of cyclopropane in
anhydrous methylene was added. After 1 h stirring at
–50 to –40°C, the reaction mixture was let to warm up
and poured into saturated NaHCO3, the organic layer
was separated, and the aqueous layer was extracted with
3 portions of chloroform. The combined organic extracts
were dried with Na2SO4, the solvent was distilled off, and
the oily viscous residue was subjected to chromatography.
EXPERIMENTAL
1
The H and 13C NMR spectra were registered on
a Bruker Avance 400 spectrometer at 400 (1H) and
100 (13C) MHz at 28°C. The chemical shifts were mea-
sured in ppm against internal TMS. Some 13C NMR
signals were assigned using the ATP experiment. The
IR spectra were run on UR-20 (in thin films or mineral
oil) and Specord 75 IR instruments (in mineral oil). The
elemental analyses of the synthesized compounds were
obtained in a Carlo Erba CHN analyzer. The GC–MS
analysis of the synthesized compounds was performed
on HewLett–Packard 5890 and Finnigan MAT SSQ 7000
instruments (electron ionization, 70 eV). The ESI– HRMS
spectra were measured on a Thermo Scientific Orbitrap
Elite instrument with direct sample injection, flow rate
3 μL/min. The samples were dissolved in acetonitrile
(1 mL), diluted 1 : 100 with 1% formic acid in aceto-
nitrile. The measurements were performed in the positive
ion mode with a resolution of 480000.
The nitrosation of diarylcyclopropanes 1a–1d and
arylcyclopropane 3 was performed with 0.2 mmol of
sulfur trioxide (method a) or sulfur trioxide dioxane com-
plex (method b) in 15 mL of CH2Cl2, 0.4 mmol of ethyl
nitrite in 15 mLof CH2Cl2, and 0.2 mmol of cyclopropane
in 10 mL of CH2Cl2. The reaction mixture was hydro-
lyzed at 20°C. The yields of isoxalines were as follows:
2a (95%), 2b (92%), 2c (93%), 2d (71%), and 4 (94%)
(method a), and 2b (100%) (method b). The physico-
chemical characteristics of the synthesized compounds
completely coincided with those reported in the literature:
2a [3], 2b [4], 2c [5], 2d [6], and 4 [7].
The nitrosation of arylcyclopropanes 5a and 5b was
performed with 0.2 mmol of sulfur trioxide (method a)
or sulfur trioxide dioxane complex (method b) in 15 mL
of CH2Cl2, 0.4 mmol of ethyl nitrite in 15 mL of CH2Cl2,
and 0.2 mmol of cyclopropane in 10 mL of CH2Cl2. The
Nitrosation of arylcyclopropanes with ethyl nitrite
in the presence of sulfur trioxide or sulfur trioxide
dioxane complex (general procedure).Afreshly prepared
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STUDY OF THE FEATURES OF THE REACTION OF ARYLCYCLOPROPANES
759
reaction mixture was hydrolyzed at –20°C (method a)
or 0°C (method b). From cyclopropane 5a we obtained
compounds 6a (59%) and 7a (19%) (method a) and 6a
(33%) and 7a (4%) (method b), and from cyclopropane
5b we obtained compounds 6b (57%) and 7b (10%)
(method a) and 6b (91%) and 7b (2%) (method b). The
physicochemical characteristics of the synthesized com-
pounds completely coincided with those reported in the
literature: 6a, 6b, 7a, and 7b [11].
1H NMR spectrum (CDCl3), δ, ppm (17a): 1.10–
1.20 m and 1.60–1.90 m (10H, HCy), 1.23 t (3H, CH3, J
7.4 Hz), 2.00 m (1H, H1Cy), 3.25 d.d (1H, H2, J 16.0,
8.3 Hz), 3.30 d.d (1H, H2, J 16.0, 3.0 Hz), 4.20 m (2H,
OCH2), 4.75 d.t (1H, H1, J 8.3, 3.0 Hz), the aromatic
proton signals overlap with the corresponding signals
1
of compound 16a. H NMR spectrum (C6D6), δ, ppm
(17a): 1.00 t (3H, CH3, J 7.0 Hz), 1.00–1.30 m and 1.60–
1.90 m (10H, HCy), 2.10 t.q (1H, H1Cy, J 11.9, 3.0 Hz),
3.23 d.d (1H, H2, J 16.1, 3.0 Hz), 3.33 d.d (1H, H2, J
16.1, 8.4 Hz), 4.02 m (2H, OCH2), 5.02 d.t (1H, H1, J
8.4, 3.0 Hz), the aromatic proton signals overlap with the
corresponding signals of compound 16a. 13C NMR
spectrum (CDCl3), δ, ppm (16a): 14.46 (CH3), 25.7,
25.9, 25.98, 26.06, 28.2, 39.47 (CCy), 41.7 (C2), 70.06
The nitrosation of 1-alkyl-2-arylcyclopropane was
performed with 0.4 mmol of sulfur trioxide (method a)
or sulfur trioxide dioxane complex (method b) in 15 mL
of CH2Cl2, 0.8 mmol of ethyl nitrite in 15 mL of CH2Cl2,
and 0.2 mmol of cyclopropane in 10 mL of CH2Cl2. The
reaction mixture was hydrolyzed at –20°C (method a) or
0°C (method b). The reaction with 1-methyl-2-phenyl-
cyclopropane (8) gave isoxalines 9 (74%) and 10 (18%)
(method a) and 9 (83%) (method b). The physicochemi-
cal characteristics of the synthesized compounds com-
pletely coincided with those reported in the literature: 9
and 10 [3].
3,5
2,6
(OCH2), 84.2 (C1), 128.2 (C
), 128.9 (C
), 131.9
arom
arom
(C4arom), 136.4 (C1arom). IR spectrum, ν, cm–1 (16a + 17a):
1695 (C=O), 1590 (NO2), 1390, 1180 (OSO2O). The mass
chromatogram contained two main peaks. Mass spec-
trum, m/z (Irel, %) (16a): 214 (3.6) [M – HOSO2OEt]+,
120 (10.9), 105 (100.0) [PhCO]+, 79 (10.9), 77 (29.1),
51 (7.3). Mass spectrum, m/z (Irel, %) (17a: 212 (100.0)
[M – HOSO2OEt–NO2]+, 183 (66.0), 170 (27.7), 158
(64.6), 141 (36.9), 128 (24.6), 115 (27.7), 105 (29.2), 77
(43.1), 51 (12.3).
The reaction with 2-cyclohexyl-1-phenylcyclopropane
12a gave compounds 13a (14%), 14a (5%), 15a (9%),
16a (35%), and 17a (20%) (method a) and 13a (4%)
and 14a (6%), 15a (2%), 16a (9%), and 17a (4%)
(method b). The physicochemical characteristics of isoxa-
lines 13a, 14a, and 15a coincided with those reported
in [18].
The reaction with 2-cyclohexyl-1-(4-iodophenyl)-
cyclopropane 12b gave compounds 13b (11%) and 14b
(13%), 15b (8%), 16b (35%), 17b (20%) (method a).
3-Cyclohexyl-5-(4-iodophenyl)-2-isoxaline. Rf
1
0.48 (eluent petroleum ether–ethyl acetate, 3 : 1). H
1-Cyclohexyl-3-oxo-3-phenylpropyl ethyl sulfate
(16a) and 1-cyclohexyl-3-(nitroimino)-3-phenylpropyl
ethyl sulfate (17a) could not be separated by column
chromatography. Rf 0.62 (eluent petroleum ether–ethyl
NMR spectrum (CDCl3), δ, ppm: 1.00–1.40 m, 1.70–
1.90 m (10H, HCy), 2.45 m (1H, H1Cy), 2.83 d.d (1H,
H4, J 16.9, 7.6 Hz), 3.37 d.d (1H, H4, J 16.9, 10.8 Hz),
5.45 d.d (1H, H5, J 10.8, 7.6 Hz), 7.07 d (2Harom, J
1
acetate, 3 : 1). H NMR spectrum (CDCl3), δ, ppm
1
8.4 Hz), 7.68 d (2Harom, J 8.4 Hz). H (C6D6), δ, ppm:
(16a): 1.00–1.20 m and 1.60–1.90 m (11H, HCy), 1.23 t
(3H, CH3, J 7.4 Hz), 3.25 d.d (1H, H2, J 17.4, 6.0 Hz),
3.54 d.d (1H, H2, J 17.4, 6.0 Hz), 4.25 m (2H, OCH2),
5.20 t.d (1H, H1, J 6.0, 4.4 Hz), 7.40–7.60 m (3Harom),
0.80–1.70 (10 H), 2.16 m (1H, H1Cy), 2.32 d.d (1H, H4,
J 16.6, 7.4 Hz), 2.71 d.d (1H, H4, J 16.6, 10.8 Hz),
5.12 d.d (1H, H5, J 10.8, 7.4 Hz), 6.86 d (2Harom, J 8.4 Hz),
7.53 d (2Harom, J 8.2 Hz). 13C NMR spectrum (CDCl3),
δ, ppm: 26.05, 29.7, 30.37, 30.41 (CCy), 37.3 (C1Cy), 43.7
(C4), 80.3 (C5), 93.5 (C4arom), 127.9 (C2arom, C6arom), 137.7
(C3arom, C5arom), 141.3 (C1arom), 155.7 (C3).
1
7.94 d (2Harom, J 7.1 Hz). H NMR spectrum (C6D6),
δ, ppm (16a): 1.00–1.30 m and 1.60–1.90 m (10H, HCy),
1.00 t (3H, CH3, J 7.0 Hz), 2.00 m (1H, H1Cy), 3.04 d.d
(1H, H2, J 17.2, 5.5 Hz), 3.53 d.d (1H, H2, J 17.2,
5.5 Hz), 4.10 q (2H, OCH2, J 7.2 Hz), 5.53 t.d (1H, H1,
J 5.5, 4.7 Hz), 7.10–7.50 m (3Harom), 7.94 d (2Harom, J
7.1 Hz). 13C NMR spectrum (CDCl3), δ, ppm (16a): 14.46
(CH3), 25.6, 25.8, 26.1, 27.4, 28.9, 39.65 (CCy), 41.4 (C2),
4-Cyclohexyl-5-(4-iodophenyl)-2-isoxaline (14b).
Rf 0.62 (eluent petroleum ether–ethyl acetate, 3 : 1). 1H
NMR spectrum (CDCl3), δ, ppm: 1.00–1.40 m, 1.50–
1.80 m (11H, HCy), 3.05 t.d (1H, H4, J 6.4, 1.6 Hz),
5.18 d (1H, H5, J 6.4 Hz), 7.05 d (2Harom, J 8.4 Hz),
7.14 br.s (1H, H3), 7.68 d (2Harom, J 8.4 Hz). 13C NMR
3,5
2,6
69.5 (OCH2), 86.0 (C1), 128.1 (C
), 128.7 (C
),
arom
arom
133.5 (C4arom), 136.4 (C1arom), 195.95 (C=O).
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 56 No. 5 2020

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GAVRILOVA et al.
spectrum (CDCl3), δ, ppm: 25.97, 25.99, 26.15, 30.66,
30.96 (CCy), 40.05 (C1Cy), 64.02 (C4), 82.7 (C5), 93.4
(C4arom), 127.5 (C2arom, C6arom), 137.8 (C3arom, C5arom), 141.4
(C1arom), 147.7 (C3). Mass spectrum, m/z (Irel, %): 355
(100.0) [M]+, 312 (25.0), 272 (27.0), 233 (40.0), 231
(30.0), 230 (42.0), 83 (63.0), 55 (77.0).
3.03 d.d (1H, H2, J 16.2, 2.9 Hz), 3.11 d.d (1H, H2, J
16.2, 8.1 Hz), 3.90 m (2H, OCH2,), 4.84 d.t (1H, H1, J
8.1, 2.9 Hz), 6.87 d (2Harom, J 8.9 Hz), 7.38 d (2Harom, J
8.9 Hz). 13C NMR spectrum (CDCl3), δ, ppm (17b): 14.5
(CH3), 25.7, 25.97, 26.0, 26.1, 28.3, 36.3 (CCy), 41.76
2,6
(C2), 70.25 (OCH2), 84.2 (C1), 99.3(C4arom), 129.8 (C
),
arom
3,5
137.8 (C1arom), 138.3 (C
). The mass chromatogram
arom
4-Cyclohexyl-5-(4-iodophenyl)-2-isoxaline (15b).
Rf 0.65 (eluent petroleum ether–ethyl acetate, 3 : 1). 1H
NMR spectrum (CDCl3), δ, ppm: 0.80–1.30 m, 1.60–
1.85 m (10H, HCy), 1.95 m (1H, H1Cy), 3.03 d.d (1H,
H4, J 16.5, 8.7 Hz), 3.26 d.d (1H, H4, J 16.5, 10.8 Hz),
contained two main peaks. Mass spectrum, m/z (Irel, %)
(16b): 340 (20.0) [M – HOSO2OEt]+, 338 (80.0), 231
(100.0) [4-I-C6H4CO]+. Mass spectrum, m/z (Irel, %)
(17b): 338 (100.0) [M – HOSO2OEt–NO2]+, 231 (80.0).
4.50 d.d.d (1H, H5, J 10.7, 8.7, 6.8 Hz), 7.40 d (2Harom
,
The reaction with 1-isopropyl-2-phenylcyclopropane
(19) gave compounds 21 (18%), 22 (19%), 23 (1%), 26
(14%), 27 (11%), 28 (5%), and 29 (4%) (method a) and
21 (12%), 22 (17%), 23 (2%), 26 (13%), 27 (18%), 28
(2%), and 29 (2%) (method b). The physicochemical
characteristics of compounds 21–23 and 26 coincided
with those reported in [18].
J 8.4 Hz), 7.75 d (2Harom, J 8.4 Hz). 13C NMR spectrum
(CDCl3), δ, ppm: 25.6, 25.8, 26.3, 28.4, 28.5 (CCy), 37.2
(C1Cy), 42.5 (C4), 86.0 (C5), 96.0 (C4arom), 128.0 (C2arom
,
C6arom), 129.5 (C1arom), 138.0 (C3arom, C5arom), 155.1 (C3).
Mass spectrum, m/z (Irel, %): 355 (100.0) [M]+, 272
(60.0), 271 (35.0), 244 (25.0), 117 (18.0). 76 (23.0), 55
(23.0).
3,4-Dimethyl-1,1-dinitro-1,2,3,4-tetrahydronaph-
thalene (27). Rf 0.55 (eluent petroleum ether–ethyl
acetate, 5 : 1). IR spectrum, ν, cm–1: 1575 (NO2), 1460,
1380. 1H NMR spectrum (CDCl3), δ, ppm: 1.22 d (3H,
CH3, J 6.9 Hz), 1.39 d (3H, CH3, J 7.0 Hz), 1.65 m (1H,
H3), 2.69 m (1H, H4), 2.76 d.d (1H, H2, J 14.0, 12.7 Hz),
3.15 d.d (1H, H2, J 14.0, 2.9 Hz), 7.35 t (1Harom, J
1-Cyclohexyl-3-(4-iodophenyl)-3-oxopropyl ethyl
sulfate (16b) and 1-cyclohexyl-3-(4-iodophenyl)-3-
(nitroimino)propyl ethyl sulfate (17b) could not be
separated by column chromatography. Rf 0.48 (elu-
ent petroleum ether–ethyl acetate, 3 : 1). IR spectrum,
ν, cm–1 (16b + 17b): 1690 (C=O), 1580 (NO2), 1400,
7.6 Hz), 7.45 m (2Harom), 7.55 t (1Harom, J 7.6 Hz). 13
C
1
1200 (OSO2O). H NMR spectrum (CDCl3), δ, ppm
NMR spectrum (CDCl3), δ, ppm: 19.7, 19.8 (CH3), 32.7,
39.7, 39.3 (C2, C3, C4), 126.8, 128.3, 128.4, 132.3, 144.2
(Carom). Found, %: C 57.68; H 5.53; N 11.03. C12H14N2O4.
Calculated, %: C 57.60; H 5.60; N 11.20.
(16b): 1.10–1.40 m and 1.70–1.90 m (11H, HCy), 1.30 t
(3H, CH3, J 7.4 Hz), 3.23 d.d (1H, H2, J 17.2, 5.8 Hz),
3.51 d.d (1H, H2, J 17.2, 5.8 Hz), 4.27 m (2H, OCH2),
5.17 t.d (1H, H1, J 5.8, 4.6 Hz), 7.61 d (2Harom, J 8.6 Hz),
1
7.86 d (2Harom, J 8.6 Hz). H NMR spectrum (C6D6),
4-Methyl-1-oxo-1-phenylpentan-3-yl ethyl sulfate
(28). Rf 0.56 (eluent petroleum ether–ethyl acetate,
5 : 1). IR spectrum, ν, cm–1: 1690 (C=O), 1600, 1390,
δ, ppm (16b): 0.80–1.70 m (10H, HCy), 0.90 t (3H, CH3,
J 7.0 Hz) 1.85 m (1H, H1Cy), 2.83 d.d (1H, H2, J 17.4,
5.5 Hz), 3.30 d.d (1H, H2, J 17.4, 5.5 Hz), 3.99 q (2H,
OCH2, J 7.0 Hz), 5.35 t.d (1H, H1, J 5.5, 5.1 Hz), 7.34 d
(2Harom, J 8.6 Hz), 7.50 d (2Harom, J 8.6 Hz). 13C NMR
spectrum (CDCl3), δ, ppm (16b): 14.5 (CH3), 25.88,
1
1200 (OSO2O). H NMR spectrum (CDCl3), δ, ppm:
1.02 t (3H, CH3, J 6.8 Hz), 1.10 t (3H, CH3, J 6.8 Hz),
1.34 t (3H, CH3, J 7.1 Hz), 2.29 quint.d (1H, H4, J 6.8,
3.9 Hz), 3.22 d.d (1H, H2, J 17.2, 6.1 Hz), 3.60 d.d (1H,
H2, J 17.2, 6.1 Hz), 4.30 q.d (2H, OCH2, J 7.1, 1.8 Hz),
5.26 t.d (1H, H1, J 6.1, 3.9 Hz), 7.51 t (2Harom, J 7.5 Hz),
25.91, 26.1, 27.5, 28.4, 39.7 (CCy), 41.4 (C2), 69.67
2,6
(OCH2), 85.8 (C1), 101.8 (C4arom), 129.5 (C
), 135.7
arom
3,5
(C4arom), 138.1 (C
), 195.4. (C=O).
7.62 t (1Harom, J 7.5 Hz), 7.95 d (2Harom, J 7.5 Hz). 13
C
arom
1H NMR spectrum (CDCl3), δ, ppm (17b): 1.10–
1.40 m and 1.70–1.90 m (10H, HCy), 1.30 t (3H, CH3,
J 7.4 Hz) 2.05 m (1H, H1Cy), 3.21 d.d (1H, H2, J 16.2,
8.0 Hz), 3.28 d.d (1H, H2, J 16.2, 3.0 Hz), 4.20 m (2H,
NMR spectrum (CDCl3), δ, ppm: 14.5 (OCH2CH3), 16.9,
17.8 (C5, C4CH3), 31.5 (C4), 39.3 (C2), 69.6 (OCH2), 86.3
(C3), 128.2 (C3arom, C5arom), 128.8 (C2arom, C6arom), 133.7
(C4arom), 136.4 (C1arom), 196.1 (C=O). Mass spectrum,
m/z (Irel, %): 174 (78.2) [M – HOSO2Et]+, 159 (45.8),
132 (100.0), 115 (13.2), 104 (44.8), 91 (10.0), 78 (12.3).
OCH2), 4.73 d.t (1H, H1, J 8.0, 3.0 Hz), 7.25 d (2Harom
,
J 8.8 Hz), 7.87 d (2Harom, J 8.8 Hz). 1H NMR spectrum
(C6D6), δ, ppm (17b): 0.80–1.70 m (10H, HCy), 0.90 t
(3H, CH3, J 7.0 Hz), 2.00 t.q (1H, H1Cy, J 11.9, 2.7 Hz),
4-Methyl-1-(nitroimino)-1-phenylpentan-3-yl
ethyl sulfate (29). Rf 0.52 (eluent petroleum ether–ethyl
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STUDY OF THE FEATURES OF THE REACTION OF ARYLCYCLOPROPANES
761
acetate, 5 : 1). IR spectrum, ν, cm–1: 1570 (NO2), 1400,
1200 (OSO2O). H NMR spectrum (CDCl3), δ, ppm:
oily residue was subjected to chromatography. The reac-
tion with cyclopropane 5a gave isoxaline 6a (94%). The
reaction with cyclopropane 8 gave isoxalines 9 (43%),
10 (26%), and 11 (7%). The reaction with cyclopropane
12a gave isoxalines 13a (8%), 14a (10%), and 15a (34%).
The reaction with cyclopropane 19 gave compounds 21
(16%), 22 (15%), 23 (1%), 24 (3%), and 25 (12%). The
reaction with cyclopropane 20 gave compounds 31 (3%),
32 (37%), 33 (5%), 34 (18%), and 35 (3%). The physico-
chemical characteristics of the synthesized compounds
completely coincided with those reported in the literature:
24 and 34 [18], 25 [19], and 33 [20].
1
1.06 t (3H, CH3, J 7.1 Hz), 1.09 t (3H, CH3, J 7.1 Hz),
1.37 t (3H, CH3, J 7.2 Hz), 2.42 quint.d (1H, H4, J 6.8,
3.3 Hz), 3.27 d (2H, H2, J 5.3 Hz), 4.23 m (2H, OCH2),
4.80 t.d (1H, H3, J 5.3, 3.3 Hz), 7.5 m (5Harom). 13C NMR
spectrum (CDCl3), δ, ppm: 14.6 (OCH2CH3), 15.4, 17.6
(C5, C4CH3), 31.5 (C4), 35.7 (C2), 70.3 (OCH2), 84.5
(C3), 127.1, 128.3, 129.1, 132.0 (Carom), 165.5 (C=N).
The reaction of 1-tert-butyl-2-phenylcyclopropane
(20) gave compounds 31 (12%), 32 (20%), 35 (5%), and
36 (4%) (method a) and 31 (7%), 32 (16%), 35 (16%),
and 36 (7%) (method b). The physicochemical charac-
teristics of compounds 31 and 32 concided with those
reported in [18].
5-Methyl-3-phenyl-2-isoxaline (11). Rf 0.65 (eluent
petroleum ether–ethyl acetate, 3 : 1). 1H NMR spectrum
(CDCl3), δ, ppm: 1.44 d (3H, CH3, J 6.2 Hz), 2.94 d.d
(1H, H4, J 16.3, 7.9 Hz), 3.44 d.d (1H, H4, J 16.3,
10.1 Hz), 4.89 d.d.q (1H, H5, J 10.1, 7.9, 6.2 Hz), 7.41 m
(3Harom), 7.68 m (2Harom). 13C NMR spectrum (CDCl3),
3,4,4-Trimethyl-3,4-dihydronaphthalen-1(2H)-one
(35). Rf 0.60 (eluent petroleum ether–ethyl acetate, 3 : 1).
1
IR spectrum, ν, cm–1: 1690 (C=O). H NMR spectrum
δ, ppm: 21.0 (CH3), 41.6 (C4), 77.5 (C5), 126.6 (C3arom
,
(CDCl3), δ, ppm: 1.07 d (3H, C3CH3, J 6.9 Hz), 1.44 s
(6H, C4CH3), 2.22 m (1H, H3), 2.55 d.d (1H, H2, J 17.4,
9.5 Hz), 3.60 d.d (1H, H2, J 17.4, 4.5 Hz), 7.31 t (1H,
H6arom, J 7.8 Hz), 7.47 d (1H, H5arom, J 7.8 Hz), 7.55 t (1H,
H7arom, J 7.8 Hz), 8.04 d (1H, H8arom, J 7.8 Hz). 13C NMR
spectrum (CDCl3), δ, ppm: 16.3 (C3CH3), 16.9, 17.8
(C4CH3), 37.45 (C4), 38.9 (C3), 43.1 (C2), 126.2, 127.0,
131.1, 134.0, 152.3 (Carom), 198.4 (C=O). Mass spectrum,
m/z (Irel, %): 188 (59.5) [M]+, 173 (100.0), 145 (47.4),
131 (39.0), 117 (21.7), 115 (14.5), 103 (10.4), 91 (11.1).
C5arom), 128.7 (C2arom, C6arom), 129.9 (C4arom), 132.2 (C1arom),
156.5 (C3). Mass spectrum (ESI–HRMS), m/z: 162.0913
[M + H]. C10H11NO. 162.0913 [M + H].
Nitrosation of arylcyclopropanes 8, 12a, and 19
with nitrosonium tetrafluoroborate in acetonitrile
(general procedure). A solution of 2 mmol of cyclopro-
pane in 5 mL of acetonitrile was added to a suspension
of 4 mmol of nitrosonium tetrafluoroborate in 5 mL of
acetonitrile at 0°C. The reaction mixture was stirred at
this temperature for 30 min, after which it was allowed to
warm up to room temperature and hydrolyzed with satu-
rated NaHCO3 (10 mL). The organic layer was separated,
and the aqueous layer was extracted with chloroform (3 ×
10 mL). The combined organic extracts were dried over
Na2SO4. The solvent was distilled off, and the viscous oily
residue was subjected to chromatography. The reaction
with cyclopropane 8 gave isoxaline 9 (90%). The reac-
tion with cyclopropane 12a gave compounds 13a (8%),
14a (10%), 15a (34%), and 18 (57%). The reaction with
cyclopropane 19 gave compounds 21 (12%), 22 (5%), 23
(1%), 26 (5%), and 30 (12%).
4,4-Dimethyl-1-oxo-1-phenylpentan-3-yl ethyl sul-
fate (36). Rf 0.56 (eluent petroleum ether–ethyl acetate,
3 : 1). 1H NMR spectrum (CDCl3), δ, ppm: 1.05 s (9H,
CH3), 1.27 t (3H, OCH2CH3, J 7.1 Hz), 3.24 d.d (1H,
H2, J 17.9, 4.8 Hz), 3.55 d.d (1H, H2, J 17.9, 5.3 Hz),
4.30 m (2H, OCH2), 5.28 t (1H, H3, J 5.0 Hz), 7.40–
7.60 m (3Harom), 7.98 d (2Harom, J 8.0 Hz). Mass spectrum,
m/z (Irel, %): 190 (40.5) [M – HOSO2Et]+, 133 (48.1), 105
(100.0), 91 (63.9), 57 (22.4), 55 (23.5).
Nitrosation of arylcyclopropanes 5a, 8, 12a, 19,
and 20 with nitrosonium tetrafluoroborate in nitro-
methane (general procedure). A solution of 2 mmol of
cyclopropane in 5 mL of nitromethane was added to a
suspension of 2 mmol of nitrosonium tetrafluoroborate in
5 mL of nitromethane at room temperature. The reaction
mixture was stirred for 1 h, hydrolyzed with saturated
NaHCO3 (10 mL), the organic layer was separated, and
the aqueous layer was extracted with chloroform (3 ×
10 mL). The combined organic extracts were dried over
Na2SO4. The solvent was distilled off, and the viscous
N-(1-cyclohexyl-3-oxo-3-phenylpropyl)acetamide
(18). Rf 0.11 (eluent petroleum ether–ethyl acetate,
5 : 1). IR spectrum, ν, cm–1: 3279 (NH), 1690 (C=O), 1650
(C=O), 1560, 1450, 1380. 1H NMR spectrum (CDCl3),
δ, ppm: 1.00–1.30 m and 1.60–1.80 m (10H, HCy),
1.88 m (1H, H1Cy), 1.97 s (3H, CH3), 3.13 d.d (1H,
H2, J 17.2, 4.9 Hz), 3.37 d.d (1H, H2, J 17.2, 4.9 Hz),
4.13 t.t (1H, H1, J 9.2, 4.9 Hz), 6.29 d (1H, NH, J
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 56 No. 5 2020

762
GAVRILOVA et al.
7. Bondarenko, O.B., Gavrilova, A.Yu., Saginova, L.G.,
Zyk, N.V., and Zefirov, N.S., Russ. J. Org. Chem.,
2009, vol. 45, p. 218.
9.2 Hz), 7.48 t (2Harom, J 7.8 Hz), 7.59 t (1Harom, J
7.2 Hz), 7.95 d (2Harom, J 7.0 Hz). 13C NMR spectrum
(CDCl3), δ, ppm: 23.4 (CH3), 25.9, 26.01, 26.2, 29.8, 30.2,
40.2 (CCy), 39.1 (C2), 51.3 (C1), 133.4 (C4arom), 128.04
https://doi.org/10.1134/S1070428009020110
2,6
(Ca3r,5om), 128.7 (C
), 136.8 (C1arom), 169.6 (C=Oamide),
8. Gazzaeva, R.A., Shabarov, Yu.S., and Saginova, L.G.,
Chem. Heterocycl. Compd., 1984, vol. 20, p. 246.
https://doi.org/10.1007/BF00515629
arom
199.7 (C=O). Mass spectrum, m/z (Irel, %): 274 (0.7)
[M + H]+, 230 (1.3), 215 (2.6), 190 (10.5), 106 (36.2),
105 (100.0). Mass spectrum (ESI–HRMS), m/z: 274.1804
[M + H]. C17H23NO2. 274.1802 [M + H].
9. Ichinose, N., Mizuno, K., Tamai, T., and Otsuji, Y.,
Chem. Lett., 1988, p. 233.
https://doi.org/10.1246/cl.1988.233
N-(4-Methyl-1-oxo-1-phenylpentan-3-yl)acetamide
(30). Rf 0.10 (eluent petroleum ether–ethyl acetate,
3 : 1). H NMR spectrum 13C(CDCl3), δ, ppm: 0.92 d
(3H, CH3, J 6.7 Hz), 0.98 d (3H, CH3, J 6.7 Hz), 1.96 s
(3H, CH3), 3.12 d.d (1H, H2, J 17.0, 4.8 Hz), 3.35 d.d
(1H, H2, J 17.0, 5.6 Hz), 4.15 m (1H, H3), 6.25 d (1H,
NH, J 8.8 Hz), 7.45 t (2H, Harom, J 8.0 Hz), 7.60 t (1H,
10. Mizuno, K., Ichinose, N., Tamai, T., and Otsuji, Y., Chem.
Lett., 1989, p. 457.
1
https://doi.org/10.1246/cl.1989.457
11. Bondarenko, O.B., Gavrilova, A.Yu., Kazantseva, M.A.,
Tikhanushkina, V.N., Nifant’ev, E.E., Saginova, L.G.,
Zyk, N.V., and Zefirov, N.S., Russ. J. Org. Chem., 2007,
vol. 43, p. 564.
H
arom, J 8.0 Hz), 7.95 d (2H, Harom, J 8.0 Hz). 13C NMR
https://doi.org/10.1134/S1070428007040136
12. Freeman, J.P., J. Org. Chem., 1961, vol. 26, p. 4190.
https://doi.org/10.1021/jo01069a002
spectrum (CDCl3), δ, ppm: 19.3, 19.7 (C4CH3, C5), 23.4
(CH3), 30.89 (C4), 39.6 (C2), 52.2 (C3), 128.1 (C4arom),
128.8 (C2arom, C3arom, C5arom, C6arom), 133.5 (C1arom), 169.8
(C=O), 199.5 (C=O).
13. Cameron, T.S., Cordes, R.E., Morris, D.G., and Mur-
ray, A.M., J. Chem. Soc. Perkin Trans. 2, 1979, p. 300.
https://doi.org/10.1039/P29790000300
ACKNOWLEDGMENTS
14. Adamopoulos, S., Boulton, A.J., Tadayoni, R., and
Webb, G.A., J. Chem. Soc. Perkin Trans. 1, 1987, p. 2073.
https://doi.org/10.1039/P19870002073
The authors are grateful to Thermo Fisher Scientific, MS
Analytics (Moscow) and personally to Prof. A.A. Makarov for
providing the mass spectrometric equipment used in this work.
15. Wieland, T. and Grimm, D., Chem. Ber., 1963, vol. 96,
p. 275.
CONFLICT OF INTEREST
The authors declare no conflict of interest.
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