Hydroxylamine Reactions with Peroxide Products of Alkenes Ozonolysis

Article abstract of DOI:10.1134/S107042801808002X

Reactions were studied of peroxide ozonolysis products obtained from linear and cyclic alkenes with hydroxylamine prepared in situ from NH₂OH·HCl by hydrogen chloride neutralization with sodium acetate. A one-pot reactions sequence was performed: alkene oxidation with ozone → reduction to a carbonyl compound with hydroxylamine → condensation of the carbonyl compound with hydroxylamine providing a possibility of direct transformation of alkenes in keto- and aldoximes excluding the stage of preparation and isolation of the carbonyl compound.

Full text of DOI:10.1134/S107042801808002X

ISSN 1070-4280, Russian Journal of Organic Chemistry, 2018, Vol. 54, No. 8, pp. 1122–1126. © Pleiades Publishing, Ltd., 2018.
Original Russian Text © Yu.V. Legostaeva, L.R. Garifullina, I.S. Nazarov, N.M. Ishmuratova, G.Yu. Ishmuratov, 2018, published in Zhurnal Organicheskoi
Khimii, 2018, Vol. 54, No. 8, pp. 1116–1120.
Hydroxylamine Reactions with Peroxide Products of Alkenes
Ozonolysis
Yu. V. Legostaevaa,* L. R. Garifullinaa, I. S. Nazarova,
N. M. Ishmuratovaa, and G. Yu. Ishmuratova
a Ufa Institute of Chemistry, Russian Academy of Sciences, pr. Oktyabrya 71, Ufa, Bashkortostan, 450054 Russia
*е-mail: legostaevayuv@yandex.ru
Received October 18, 2017
Abstract—Reactions were studied of peroxide ozonolysis products obtained from linear and cyclic alkenes
with hydroxylamine prepared in situ from NH2OH·HCl by hydrogen chloride neutralization with sodium
acetate. A one-pot reactions sequence was performed: alkene oxidation with ozone → reduction to a carbonyl
compound with hydroxylamine → condensation of the carbonyl compound with hydroxylamine providing a
possibility of direct transformation of alkenes in keto- and aldoximes excluding the stage of preparation and
isolation of the carbonyl compound.
DOI: 10.1134/S107042801808002X
Ozonolysis splitting is one of efficient and
environmentally friendly oxidation methods widely
utilized both in the industry and in the fine organic
synthesis. Ozonolysis reaction and subsequent
transformations of the formed peroxide compounds are
well explored, and the reducers like Me2S, PPh3,
NaBH4 are now traditional and are actively applied in
converting alkene substrates in carbonyl compounds
and alcohols [1]. Yet the application of N-containing
compounds both directly at the ozonation and in
further treatments of the arising peroxides is a topical
issue. The use of hydroxylamine hydrochloride for
treating the peroxide products of olefins ozonolysis
was formerly limited to several examples, all reactions
were carried out in MeOH, and depending on the
substrate nature the resulting substances were
aldehydes [2], aldoxime [3], or ester [1]. It was found
later that the use of NH2OH·HCl in ozonolysis–
reduction reactions depending on the applied solvent
afforded carboxylic acids [4, 5] or esters [6, 7] forming
either in an individual state of in mixtures with oximes
or nitriles and resulting from the sequence of
transformations aldehyde → aldoxime → nitrile →
carboxylic acid/ester.
The goal of this study is the investigation of the
reaction of peroxide alkene ozonolysis products with
hydroxylamine proper obtained in situ by neutralizing
the hydrogen chloride with sodium acetate. We
selected as initial compound alkenes with a terminal
double bond monosubstituted non-1-ene 1, undec-10-
enoic acid 2, its methyl ester 3, and 10-undecen-1-ol 4,
and also optically active trisubstituted alkenes: (–)-α-
pinene 5, (+)-3-carene 6, (S)-(–)-limonene 7.
The products of ozonation in methanol (0°С) of non-
1-ene 1 when treated with molar 3.5-excess of the
mixture NH2OH·HCl–AcONa, 1 : 1.5, afforded a
mixture of oxime 8 and ester 9, 1.5 : 1 (Scheme 1).
It is known [1, 8] that zwitter-ions are stabilized in
methanol owing to the formation of methoxyhydroper-
oxides. The formation under these conditions of oxime 8
is logically understood as the reduction of the intermediate
peroxide 10 to aldehyde 11, whose condensation with
Scheme 1.
1. O3, MeOH, 0oC
2. NH2OH HCl_AcONa, 1 : 1.5
N
+
OH
CO2Me
1.5 : 1
1
8
9
1122

HYDROXYLAMINE REACTIONS WITH PEROXIDE PRODUCTS OF ALKENES OZONOLYSIS
1123
Scheme 2.
NH2OH
NH2OH
_H2O
O
8
11
OOH
OMe
O3, MeOH
1
AcOH_AcONa
_H2O
10
9
Scheme 3.
R
NOH
1. O3, MeOH, 0oC
2. NH2OH HCl_AcONa, 1 : 1.5
12_14
R
+
2_4
CH(OMe)2
R
15_17
R = CO2H (2, 12, 15), CO2Me (3, 13, 16), CH2OH (4, 14, 17).
hydroxylamine provides aldoxime 8. The formation of
ester 9 may be evidently due to the sensitivity of
hydroperoxide 10 to pH of the environment and its
dehydration under the conditions of the acetate buffer
formation (Scheme 2).
products: oximes 12–14 and acetals 15–17 with the
prevalence of the latter (12–15 1 : 1.7, 13–16 1 : 1.5,
14–17 1 : 2) (Scheme 3).
The presence of functional groups essentially
affects the structure of intermediate peroxides and
consequently the structure of final reaction products.
When a proton-donor is present in the alkene
molecule, it takes part in zwitter-ion stabilization [9].
Apparently, the peroxides formed from alkenes 2–4 are
less prone to dehydration, therefore under the reaction
conditions they are reduced to aldehydes that further
are transformed in oximes 12–14 and acetals 15–17.
The presence of substituents in the substrate
molecule somewhat changes the transformation
process of the peroxide products. For instance, at
treating with NH2OH the ozonolysis products of undec-
10-enoic acid 2, its methyl ester 3, and 10-undecen-1-
ol 4 were reduced into the corresponding aldehydes
which were isolated as a mixture of condensation
Scheme 4.
HO
N
1. O3, MeOH, 0oC
2. NH2OH HCl_AcONa, 1 : 1.5
N
OH
(_)-5
18, 80%
1. O3, MeOH, 0oC
2. NH2OH HCl_AcONa, 1 : 1.5
N
OH
N
HO
6
19, 75%
1. O3, MeOH, 0oC
2. NH2OH HCl_AcONa, 1 : 1.5
NOH
NOH
20, 53%
7
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LEGOSTAEVA et al.
1124
Formerly at the use of hydroxylamine
1.5 (Electrospray ionization) and 2.5 (CIAP) L/min.
Elemental analysis was carried out on a СHNS-
analyzer Euro EA 3000. TLC monitoring was
performed on SiO2 Sorbfil (Russia). In column
chromatography SiO2 (70–230) Lancaster (England)
was used. Ozonizer capacity was 40 mmol О3/h.
hydrochloride for processing peroxides obtained by
ozonation of (–)-α-pinene 5 and (+)-3-carene 6 in
methanol we isolated in a good yield bifunctional
derivatives containing an ester and a ketoxime groups
[10]. At the reduction of peroxides prepared from
monoterpenes 5–7 in the same conditions with
hydroxylamine proper we isolated optically active
dioximes 18–20 (Scheme 4).
Alkenes ozonolysis and treatment of the reaction
mixture with hydroxylamine. General procedure.
Through a solution of 10.0 mmol of alkene in 25 mL
of anhydrous methanol at 0°С was bubbled ozone-
oxygen mixture till 10 mmol of ozone was consumed.
The reaction mixture was flushed with argon. At 0ºС a
mixture of 2.44 g (35.0 mmol) of NH2OH·HCl and
4.10 g (50 mmol) of AcONa was added to the
ozonolysis products and stirring was continued till
peroxides disappearance (negative iodine-starch test).
The solvent was distilled off, the residue was dissolved
in CHCl3 (150 mL), washed with brine (4 × 35 mL),
dried with Na2SO4, and evaporated.
Ald- and ketoximes are valuable intermediate
products of the synthetic organic chemistry widely
used in the chemical industry [11], and they are
traditionally prepared by treating aldehydes and
ketones with mineral salts of hydroxylamine (for
instance, NH2OH·HCl or NH2OH·H2SO4) [12, 13]. In
this case at the treating ozonolysis products with
hydroxylamine generated in situ from the
hydrochloride a one-pot sequence is performed: alkene
oxidation with ozone → reduction to a carbonyl
compound with hydroxylamine → condensation of the
carbonyl compound with hydroxylamine providing a
possibility of direct transformation of alkenes in keto-
and aldoximes excluding the stage of preparation and
isolation of the carbonyl compound.
Ozonolysis of non-1-ene (1). After chromatogra-
phing of 0.96 g of reaction mixture (petroleum ether–
methyl tert-butyl ether, 10 : 1→1 : 2) we obtained
0.37 g (23%) of methyl octanoate 9 [14] and 0.56 g
(39%) of (1Е)-octanal oxime 8 (mp 57–58°С) [7].
Thus at treating with hydroxylamine the peroxide
ozonolysis products obtained from linear and cyclic
alkenes the reduction prevailingly furnished aldehydes/
ketones isolated depending on the substrate as keto-
and aldoximes or acetals.
Ozonolysis of undec-10-enoic acid (2). After
chromatographing of 1.91 g of reaction mixture
(petroleum ether–methyl tert-butyl ether, 10 : 1→1 : 1,
MеОН) we obtained a mixture of 0.71 g (35%) of
oximacid 12 and 1.2 g (58%) of acid 15.
EXPERIMENTAL
(10E)-10-(Hydroxyimino)decanoic acid (12). Oily
substance, Rf 0.22 (petroleum ether–ethyl acetate, 1 : 2).
Mass spectrum, m/z (Irel, %): [M + H]+ 202 (28.5). IR
and NMR spectra are identical to the published data
[15].
IR spectra were recorded on a spectrophotometer IR
Prestige-21 (Fourier Transform Spectrophotometer –
Shimadzu). NMR spectra were registered on a high
resolution spectrometer Bruker Avance III 500
[operating frequencies 500 (1Н), 125.76 (13С) MHz] in
CDCl3, internal reference TMS. GLC was performed
on a chromatograph Chrom-5 [column 1.2 m long,
stationary phase SE-30 (5%) on the carrier Chromaton
N-AW-DMCS (0.16–0.20 mm), working temperature
50–300°С], carrier gas helium. The optical rotation
was measured on a polarimeter Perkin Elmer 241-MC.
Mass spectra were taken on an instrument LCMS-2010
EV (Shimadzu) (injection sample admission, eluent
acetonitrile–water, 95 : 5, flow rate 0.1 mL/min) in the
mode of positive and negative ions registration at the
capillary potential 4.5 and –3.5 kV. Interface (CIAP)
temperature 250°С, oven temperature 200°С, vaporizer
temperature 230°С. Flow rate of nebulizing gas (nitrogen)
10,10-Dimethoxydecanoic acid (15). Oily
substance, Rf 0.27 (petroleum ether–ethyl acetate, 1 : 2).
1
IR spectrum (KBr), ν, cm–1: 2853 (О–СН3). Н NMR
spectrum, δ, ppm: 1.20–1.70 m (14H, С3–9Н2), 2.25–
2.32 m (2H, С2Н2), 3.45 s (6H, 2OСН3), 3.95 t (1H,
С10Н, J 6.6 Hz), 9.75 br.s (1H, CO2H). 13С NMR
spectrum, δ, ppm: 24.58 t (С8Н2), 24.80 t (С7Н2), 25.70
t (С6Н2), 26.22 t (С5Н2), 27.45 t (С4Н2), 29.34 t
(С3Н2), 31.24 t (С9Н2), 34.01 t (С2Н2), 55.84 q
(2OСН3), 108.83 d (С10Н), 179.70 s (CO2H). Found,
%: C 61.85; H 10.08. C12H24O4. Calculated, %: C
62.04; H 10.41.
Ozonolysis of methyl undec-10-enoate (3). After
chromatographing of 2.10 g of reaction mixture
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 54 No. 8 2018

HYDROXYLAMINE REACTIONS WITH PEROXIDE PRODUCTS OF ALKENES OZONOLYSIS
1125
(petroleum ether–methyl tert-butyl ether, 10 : 1→1 : 1,
MеОН) we obtained 0.82 g (38%) of compound 13
and 1.23 g (55%) of compound 16.
108.74 d (С10H). Found, %: C 66.72; H 12.30.
C12H26O3. Calculated, %: C 66.01; H 12.00.
Ozonolysis of (–)-α-pinene (5). After chromatogra-
phing of 1.97 g of reaction mixture (petroleum ether–
methyl tert-butyl ether, 10 : 1→1 : 1, MеОН) we
obtained 1.58 g (80%) of oxime 18.
Methyl (10E)-10-(hydroxyimino)decanoate (13).
Oily substance, Rf 0.33 (petroleum ether–ethyl acetate,
1 : 2). Mass spectrum, m/z (Irel, %): [M + H]+ 216
(100). IR and NMR spectra are identic to the published
data [16].
(1Е)-{(1R,3R)-3-[(1Е)-N-Hydroxyethanimidoyl]-
2,2-dimethylcyclobutyl}acetaldehyde oxime (18) [4].
Oily substance, Rf 0.61 (petroleum ether–ethyl acetate,
1 : 1). [α]2D0 –8° (c 1.64, CHCl3). IR spectrum (KBr), ν,
Methyl 10,10-dimethoxydecanoate (16). Oily
substance, Rf 0.39 (petroleum ether–ethyl acetate, 1 : 2).
IR spectrum (KBr), ν, cm–1: 2856 (О–СН3), 1730
1
cm–1: 1601 (C=N). Н NMR spectrum, δ, ppm: 0.89,
1
(СО2СН3). Н NMR spectrum, δ, ppm: 1.20–1.60 m
1.22 s (6Н, 2СН3), 1.82 s (3Н, CH3C=N), 1.90–2.04 m
(2Н, СН2), 2.08 m (1Н, CH), 2.13–2.25 m (2Н,
СН2СН=N), 2.61 m (1Н, CHC=N), 7.35 m (1Н,
СН2СН=N), 8.70–9.30 br.s (2H, 2NОН). 13С NMR
spectrum, δ, ppm: 14.50 q (CH3C=N), 17.02 q (CH3C),
24.60 t (CHCH2CH), 30.27 t (CH2CH=N), 30.39 q
(CH3C), 39.67 s (C), 42.81 d (CH), 47.97 d (CHC=N),
151.33 d (CH=N), 157.98 s (C=N). Mass spectrum, m/z
(Irel, %): [M + H]+ 199 (100). Found, %: C 60.12; H
9.13; N 14.25. C10H18N2O2. Calculated, %: C 60.58; H
9.15; N 14.13.
(14H, С3–9Н2), 2.24 t (2H, C2H2, J 7.5 Hz), 3.61 s (6H,
2OCН3), 3.82 s (3H, CO2CH3), 3.93 t (1H, C10H, J
6.5 Hz). 13С NMR spectrum, δ, ppm: 24.78 t (С3H2),
27.49 t (С4H2), 28.80 t (С5H2), 28.90 t (С6H2), 29.26 t
(С7H2), 29.44 t (С8H2), 32.50 t (С9H2), 33.80 t (С2H2),
51.18 q (CO2CH3), 51.38 q (2OCH3), 108.67 d (C10H),
174.33 s (CO2CH3). Found, %: C 64.01; H 10.20.
C13H26O4. Calculated, %: C 63.38; H 10.64.
Ozonolysis of 10-undecen-1-ol (4). After chroma-
tographing of 1.92 g of reaction mixture (petroleum
ether–methyl tert-butyl ether, 10 : 1→1 : 1, MеОН) we
obtained 0.63 g (34%) of oxime 14 and 1.2 g (55%) of
compound 17.
Ozonolysis of (+)-3-carene (6). After chromatogra-
phing of 1.57 g of reaction mixture (petroleum ether–
methyl tert-butyl ether, 10 : 1→1 : 1, MеОН) we
obtained 1.49 g (75 %) of oxime 19.
(10E)-10-Hydroxydecanal oxime (14). Oily sub-
stance, Rf 0.17 (petroleum ether–ethyl acetate, 1 : 2).
(1Е)-{(1R,3S)-3-[(2Е)-2-(Hydroxyimino)propyl]-
2,2-dimethylcyclopropyl}acetaldehyde oxime (19)
[6]. Oily substance, Rf 0.44 (petroleum ether–ethyl
acetate, 1 : 1). [α]2D0 –20° (c 0.08, CHCl3). IR spectrum
1
IR spectrum (KBr), ν, cm–1: 1600 (С=N). Н NMR
spectrum, δ, ppm: 1.20–1.43 m (12H, C3–8H2), 1.52–
1.56 m (2H, C9H2), 2.13–2.20 m (2H, C2H2), 3.60–3.65
m (2Н, C10H2), 5.25 br.s (1Н, ОН), 6.65 br.s (1Н,
NOH), 7.35 t (1H, C1H, J 6.2 Hz). 13С NMR spectrum,
δ, ppm: 25.80 t (С8H2), 26.46 t (С7H2), 27.53 t (С6H2),
28.98 t (С5H2), 29.03 t (С4H2), 29.21 t (С2H2), 29.34 t
(С3H2), 31.53 t (С9H2), 62.89 t (С10H2), 152.22 d
(C1H). Mass spectrum, m/z (Irel, %): [M + H]+ 188
(100). Found, %: C 64.28; H 11.84; N 7.21.
C10H21NO2. Calculated, %: C 64.13; H 11.30; N 7.48.
1
(KBr), ν, cm–1: 1598 (C=N). Н NMR spectrum, δ,
ppm: 0.76–0.94 m (2Н, 2СН), 0.94, 0.99 s (6Н,
2CH3C), 1.94 s (3Н, СН3C=N), 2.13–2.25 m (8Н,
4СН2), 7.43 t (1Н, СН2СН=N). 13С NMR spectrum, δ,
ppm: 13.64 q (CH3C=N), 14.82 q (CH3C), 14.94 q
(CH3C), 17.22 s (C), 21.12 d (CHCH2C), 22.76 d
(CHCH2CH), 25.29 t (CH2CH=N), 30.74 t (CH2C=N),
151.16 d (CH=N), 158.46 s (C=N). Mass spectrum, m/z
(Irel, %): [M + H]+ 199 (91). Found, %: C 60.39; H
9.38; N 14.19. C10H18N2O2. Calculated, %: C 60.58; H
9.15; N 14.13.
10,10-Dimethoxydecan-1-ol (17). Oily substance,
Rf 0.23 (petroleum ether–ethyl acetate, 1 : 2). IR
spectrum (KBr), ν, cm–1: 3500 (ОН), 2855 (О–СН3).
1Н NMR spectrum, δ, ppm: 1.20–1.43 m (14H,
C2
(1Е,3S)-3-[(3Z)-3-(Hydroxyimino)butyl]-4-
methylpent-4-enal oxime (20). Through a solution of
1.1 g (8.09 mmol) of (S)-(–)-limonene 7 in a mixture
of 20 mL of cyclohexane and 0.6 mL of anhydrous
methanol at 2°С was bubbled ozone-oxygen mixture
till 7.4 mmol of ozone was consumed. The reaction
mixture was flushed with argon. The cyclohexane
–8H2), 1.49–1.53 m (2H, C9H2), 3.15 br.s (1H, OH),
3.43 s (6H, 2CH3), 3.50–3.55 m (2H, C1H2), 4.65 t
(1H, C10H, J 6.6 Hz). 13С NMR spectrum, δ, ppm:
25.60 t (С8H2), 26.00 t (С7H2), 28.89 t (С5H2), 29.14 t
(С6H2), 29.21 t (С3H2), 29.26 t (С4H2), 32.53 t (С2H2),
34.04 t (С9H2), 55.85 q (2ОCH3), 62.84 t (С1H2),
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LEGOSTAEVA et al.
1126
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and Tolstikov, G.A., Russ. J. Org. Chem., 2014, vol. 50,
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layer was decanted. At 0°С 20 mL of anhydrous
methanol and a mixture of 1.79 g (25.72 mmol) of
NH2OH·HCl and 3.01 g (36.75 mmol) of AcONa was
added, the reaction mixture was stirred at room
temperature till peroxides disappearance (negative
iodine-starch test). The solvent was distilled off, the
residue was dissolved in CHCl3 (150 mL), washed
with brine (4 × 35 mL), dried with Na2SO4, and
evaporated. After chromatographing of 1.21 g of
reaction mixture (petroleum ether–methyl tert-butyl
ether, 10 : 1→1 : 1, MеОН) yield 0.77 g (53%). Oily
substance, Rf 0.51 (petroleum ether–ethyl acetate, 1 : 1).
1
IR spectrum (KBr), ν, cm–1: 1610 (C=N). Н NMR
spectrum, δ, ppm: 1.13–1.30 m (2Н, СН2), 1.65 s (3H,
CH3), 1.82 s (3H, CH3), 2.00–2.18 m (4Н, 2СН2), 2.20–
2.30 m (1Н, СН), 4.60–4.90 m (2Н, СН2=C), 6.25–
6.30 m (1Н, CH=NOH), 8.20–8.90 br.s (2H, 2NОН).
13С NMR spectrum, δ, ppm: 13.68 q (CH3C=N), 18.20
q
(CH3CCH2), 28.41
t
(CH2CHC), 33.00
t
(CH2CH=N), 33.41 t (CH2C=N), 43.94 d (CH3CCH),
113.20 t (C=CH2), 145.26 s (C=CH2), 150.62 d
(CH=N), 158.59 s (C=N). Mass spectrum, m/z (Irel, %):
[M + H]+ 199 (55.4). Found, %: C 60.20; H 8.98; N
14.21. C10H18N2O2. Calculated, %: C 60.58; H 9.15; N
14.13.
ACKNOWELEDGMENTS
The study was performed using the equipment of
the Center of Joint usage “Chemistry” of Ufa Institute
of Chemistry, Russian Academy of Sciences.
11. Allen, C.L. and Williams, J.M.J., Chem. Soc. Rev.,
2011, vol. 40, p. 3405.
12. Allen, C.L., Davulcuand, S., and Williams, J.M.J., Org.
Lett., 2010, vol. 12, p. 5096.
13. Pohjakallio, A. and Pihko, P.M., Chem. Eur. J., 2009,
vol. 15, p. 3960.
14. Ishmuratov, G.Yu., Legostaeva, Yu.V., Botsman, L.P.,
Muslukhov, R.R., Yakovleva, M.P., and Talipov, R.F.,
Vestn. Bashkir. Univer., 2009, vol. 1, p. 27.
The study was partially financially supported by the
Russian Foundation for Basic Research (grant no. 17-
03-01050 А).
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