Oxidative nitration of mononitroalkanes in a system sodium nitrite-polyhaloalkane

Article abstract of DOI:10.1134/S1070428007050028

In reaction of nitroethane lithium salt with sodium nitrite in DMSO, DMF or HMPA involving polyhaloalkanes 1,1-dinitroethane formed in a high yield. The highest yield was obtained with bromo-and iododerivatives. The reaction fits to a kinetic equation of over all second order: the first with respect to the nitroethane anion, and the first in polyhaloalkane. The rate constants of the process are linearly dependent on the electron affinities of the perhaloalkanes molecules. Nauka/Interperiodica 2007.

Full text of DOI:10.1134/S1070428007050028

ISSN 1070-4280, Russian Journal of Organic Chemistry, 2007, Vol. 43, No. 5, pp. 646−651. © Pleiades Publishing, Ltd., 2007.
Original Russian Text © N.A. Petrova, M.B. Shcherbinin, A.G. Bazanov, I.V. Tselinskii , 2007, published in Zhurnal Organicheskoi Khimii, 2007, Vol. 43,
No. 5, pp. 652−657.
Dedicated to Professor V.A.Ostrovskii on occasion of his sixtieth birthday
Oxidative Nitration of Mononitroalkanes in a System
Sodium Nitrite-Polyhaloalkane
N. A. Petrova, M. B. Shcherbinin, A. G. Bazanov, and I. V. Tselinskii
St. Petersburg State Technological Institute, St. Petersburg, 190013 Russia
e-mail: ivts@tu.spb.ru
Received December 20, 2006
Abstract—In reaction of nitroethane lithium salt with sodium nitrite in DMSO, DMF or HMPA involving
polyhaloalkanes 1,1-dinitroethane formed in a high yield. The highest yield was obtained with bromo- and
iododerivatives. The reaction fits to a kinetic equation of overall second order: the first with respect to the nitroethane
anion, and the first in polyhaloalkane. The rate constants of the process are linearly dependent on the electron
affinities of the perhaloalkanes molecules.
DOI: 10.1134/S1070428007050028
silver salt in the oxidative nitration with silver nitrate
[10], and a multistage process in the ter Meer reaction
of 1-nitro-1-chloroalkanes with sodium nitrite [11].
The procedures for mononitroalkanes nitration into
gem-dinitroalkanes known now belong as a rule to ion-
radical processes since they include a stage of a single-
electron transfer (SET) [1, 2]. Nitroalkanes in alkaline
media give nitrocarbanions that are sufficiently active
electron-donors with respect to acceptors of diverse
character: molecular oxygen [3], aromatic nitro com-
pounds [4–6], polynitro- and halonitroalkanes [2, 7]. As
a result of the single-electron oxidation with these ac-
ceptors the nitrocarbanions form highly reactive nitro-
alkyl radicals. These radicals either undergo recombina-
tion with other radicals present in the system (oxidation
products of other ions) (path a), or react with nucleophilic
agents to form anion-radicals [8] (path b). The latter in
the presence of single-electron oxidants can convert into
α-substituted nitroalkanes that in event of terminal nitro
compounds provide anions (Scheme 1).Achain reaction
mechanism occurs frequently in the case b.
Therefore the development of new efficient synthetic
procedures for gem-dinitroalkanes is desirable, in
particular, by means of oxidative nitration of mononitro-
alkanes applying more available oxidants. It is presum-
able that geminal dinitro compounds can form in oxida-
tion of nitrocarbanions in the presece of excess nitrite ion.
A persulfate dianion is a well-known reagent capable
of oxidating nitrocarbanions into nitroalkyl radicals in
a water environment [12, 13]. Just at the use of this
oxidant an intermediate formation of nitroalkyl radicals
was proved [14, 15]. It is curious in this connection why
in [12] was stated that no formation of gem-dinitroalkanes
occurred in oxidation of nitroalkanes salts with am-
monium persulfate in the presence of sodium nitrite.
Therefore we carried out a thorough investigation of
oxidation under the said conditions of nitroethane,
1-nitrobutane, and 2-nitropropane alkali metal salts. We
established spectrophotometrically that from the nitro-
ethane and 1-nitrobutane gem-dinitroalkanes formed in
15 and 18% yield respectively. Yet the main products of
The existing methods of 1,1-dinitroalkanes prepara-
tion from mononitroalkanes possess significant dis-
advantages, like the formation of hazardous side products
(trinitromethane salts) in nitration with tetranitromethane
in the presence of bases [9], the application of expensive
Scheme 1.
а,
X
_
B
_
B
RCHNO2
RCHXNO2
RCH2NO2
RCXNO2
_e
RCHNO2_
b,
BH+
BH+
RCHXNO2_
X
_e
646

OXIDATIVE NITRATION OF MONONITROALKANES
647
Scheme 2.
_
_
RC CR
_HNO2 O2N NO2
RR'C CRR'
RR'C CRR'
O2N NO2
RR'CNO2
R' = H
_e
O2N NO2
RR'CNO2
_
N O
HO_, H2O
RCHNO2
R = Me, R' = H
RR'CH O
Me
Me
Me
this reaction were carbonyl compounds and trans-
formation products of trimer and dimer character respec-
tively: 3,4,5-trimethylisoxazole from 1-nitroethane and
4-nitro-4-octene from 1-nitrobutane, the product of
nitrous acid elimination from the intermediately formed
4,5-dinitrooctane.
oxidation in DMSO [17]. The oxidative action of the
tetrachloro-methane consists in an electron capture from
the 2-nitro-propane anion to form 2-nitropropyl radical.
Inasmuch as the tetrachloromethane is widely available
its application as oxidant merits attention.
In oxidation of nitroethane lithium salt with tetra-
chloromethane in the presence of a double excess of sodi-
um nitrite in DMSO we obtained 1,1-dinitroethane in 35%
yield. The discovered reaction of oxidative nitration is sen-
sitive to the solvent character: It proceeds only in aprotic
bipolar solvents DMSO, DMF, and HMPA (Table 1)
confirming the above suggestion of a considerable influ-
ence of specific solvation on the reaction under study.
The oxidation of 2-nitropropane anion with ammon-
ium persulfate in the presence of a double excess of
NaNO2 gave rise to 2,3-dimethyl-2,3-dinitrobutane (35%)
and acetone (30%) like in the process of oxidative
dimerization of nitroalkanes salts without sodium nitrate
[12].
The low yield of gem-dinitro compounds from the
primary mononitroalkanes is understandable taking into
account that under the given conditions the reaction
mixture besides the nitrite ion contains also other nucleo-
philic agents: the initial nitrocarbanion, hydroxy ion, and
water that successfully compete with the nitrite ion for
the nitroalkyl radicals (Scheme 2). Therewith the reaction
with the two latter nucleophiles results in the formation
of carbonyl compounds and consequently of trialkyl-
isoxazoles [13]. This suggestion is well consistent with
numerous data on carbonyl compounds formation as final
or side products in nitrocarbanions oxidation in water
environment [3, 12, 13]. Therefore the application of
hydroxy-containing solvents is hardly feasible.
The result of the reaction depends besides to a sig-
nificant extent on the solubility of the nitroalkane salt in
the applied solvent. For instance, at the use of dioxane
and acetonitrile where the nitroethane lithium salt is near-
ly insoluble only traces of gem-dinitroethane were found.
The insufficiently high yield of the nitromethane in
DMSO (35%) was presumably due to the low efficiency
Table 1. Effect of solvent on the yield of 1,1-dinitroethane in
oxidative nitration of nitroethane lithium salt in a system sodium
nitrite–tetrachloromethane, CH3CHNO2Li : CCl4 : NaNO2 =
1:2:3
Solvent
DMSO
DMSO–H2O, 7:1
DMSO–H2O, 6:1
DMSO–H2O, 2:1
HMPA
Yield, %
Time, ha
Suitable media with a minimum number of nucleo-
philes competing for the nitroalkyl radical and therefore
with minimum opportunities for the side reactions are
aprotic bipolar solvents. Since in these solvents lacks
the specific solvation of mononitrocarbanions prone to
hydrogen bonds formation with the hydroxy-containing
solvents [16] lacks and thanks to this circumstance the
energy expenditure decreases for desolvation in the
course of single-electron oxidation it is conceivable that
milder organic electron-acceptors might be applied.
Tetrachloro-methane may be used like such reagent as is
shown by an example of 2-nitropropane lithium salt
35
35
27
21
22
0.3
1
2
3.5
0.5
2
DMF
21
Dioxane–H2O, 7:1
Acetonitrile
Ethanol
Trace
Trace
0
3
3
10
a Optimum reaction time is presented determined by spectrophoto-
metric monitoring of 1,1-dinitroethane accumulation.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 43 No. 5 2007

PETROVA et al.
648
Table 2. Yield of 1,1-dinitroethane in oxidative nitration of
nitroethane lithium salt in a system sodium nitrite–
polyhaloalkanea, DMSO, 25°C, CH3CHNO2Li:RX:NaNO2 =
1:2:3
a formation of a stable ion-radical. This path is less
favorable by energy and as a rule is more difficultly
attained [19]. Therefore the presence of stabilizing factors
(a fluorine atom [21] and a phenyl ring [22]) reduced the
reactivity of the oxidant. Thus the factors favoring the
dissociative character of the electron capture by the
acceptor increase the efficiency of the latter in the
oxidative nitration.
Haloalkane Reaction time, min Yield, %b
−E1/2, V [18]
CBr4
CBrCl3
CI4
3
5
86
73
80
53
35
24
21
6
0.30
–
–
30
20
20
20
45
60
C2Br6
CCl4
0.68
0.78
0.62
–
To establish the quantitative relation between the
electron-acceptor properties of the oxidant and its
efficiency and to refine the suggested scheme of the
process we studied the kinetics of the nitroethane lithium
salt reaction with sodium nitrite in the presence of a series
of active polyhaloalkanes in DMSO. In keeping with the
suggested scheme the process involves an electron
transfer from the nitrocarbanion to the acceptor
(polyhaloalkane) leading to the formation of nitroalkyl
radical that can react both with nitrite ion to give the
target product and with nitroalkane anion to produce
2,3-dinitrobutane which also is found in the reaction
products. We exclude the possibility of the reaction to
proceed via successive halogenation of the nitroethane
and halogen substitution by the nitrite ion. This pathway
requires either appearance of a halogen atom by
polyhaloalkane decomposition along a less enegetically
favorable route into a halogen radical and carbanion, or
a successful competition with the excess nitrite of a halide
anion arising in situ in the stage of addition to the
nitroalkyl radical.
C2Cl6
C2Br2F4
CHI3
0.49
a
In the presence of halogen compounds listed further (compound
and −E1/2, V, value [18]) 1,1-dinitroethane did not form in 24 h
under common conditions: CH2I2, 1.12; CCl3F, –; CHCl3, 1.67;
CH2Cl2, 2.33; (CFCl2)2, –; PhCCl3, 0.68; C6Cl6, 1.44.
b Yield measured by spectrophotometry.
of CCl4, therefore we tested the application in this
reaction of other polyhaloalkanes as oxidation agents.
As seen from Table 2, the oxidative nitration of the
nitroethane lithium salt with sodium nitrite occurred
successfully not only in the presence of tetrachloro-
methane, but also with other polyhaloalkanes. The
highest yield (up to 86%) was attained at the use of
bromo- and iododerivatives.
The efficiency of polyhaloalkanes in the reaction in
question changed in parallel with the halfwave potential
of their polarographic reduction.
The radical character of the process is indicated by
the influence of the UV irradiation and of oxygen. The
irradiation with a strong source (a mercury lamp PRK-4)
considerably accelerated the reaction, and the saturation
of the solution with oxygen notably reduced the yield of
1,1-dinitroethane. The active nitroalkyl radicals apparent-
ly reacted with oxygen to yield peroxy radicals that result-
ed in side products [6]. Therefore all experiments were
carried out using deoxygenated solutions.
The interaction of polyhaloalkanes with electron-
donors is known to occur by “dissociative electron
capture”) [19].
.
RX + e J R + X −
The electron affinity of an acceptor molecule EA(RX)
depends on the electron affinity of the radical departing
.
as anion ΕA(X ), on the solvation enthalpy of this anion
(ΔHs), and also on the strngth of the broken bond D(R–
The studied reaction is described by a kinetic equation
of overall second order: first order in nitroethane anion
and first order in polyhaloalkane. The reaction order is
zero with respect to nitrite ion thus indicating that this
reagent is not involved in the rate-determining stage of
the process. Inasmuch as the radical species are very
active the limiting stage is evidently the first one,
involving the electron transfer from the nitrocarbanion
to the polyhaloalkane. Therefore the kinetic data provide
the rate constant of this stage only (k). The experimental
rate constants (Table 3) are apparent values for they do
X) [20].
.
(1)
ΕA(RX) = ΕA(X ) + ΔHs – D(R–X)
Energy of bond rupture for C–Βr and C–I bonds is
considerably less than that for C–Cl (Table 2) resulting
in the higher reactivity of the corresponding electron
acceptors.
When the molecule contains fragments capable of
unpaired electron stabilization, another direction is
possible for the acceptor interaction with the electron:
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 43 No. 5 2007

OXIDATIVE NITRATION OF MONONITROALKANES
649
Table 3. Parameters of electron affinity and reaction rate between polyhaloalkanes and nitroethane lithium salt (DMSO,
25°C)
ΕA(X⋅ ) [19,
23], kcal mol−1
77.6
ΔHs [24],
ΔG≠,
D(R–X) [23],
kcal mol−1
49.7
EA(RX),
kcal mol−1
65.9
Polyhaloalkane
X
−logk
kcal mol−1
kcal mol−1
11.19
11.57
12.09
12.12
12.45
12.50
12.96
13.09
CBr4
CBrCl3
CI4
C2Br6
CCl4
C2Cl6
C2Br2F4
CHI3
38
38
33
38
40
40
38
33
0.36
0.60
1.02
1.04
1.28
1.32
1.66
1.75
Βr
Βr
I
77.6
70.6
77.6
83.2
83.2
77.6
70.6
55.8
44.2
–
73.3
73.7
69.6
55.0
59.8
59.4
59.0
49.9
51.6
50.7
49.0
Βr
Cl
Cl
Βr
I
not take into account the possible reagents association
into ion pairs; still they may be used in approximate
calculations and correlations with indication of certain
limits.
Initial reagents and solvents were purified by standard
procedures [27], their characteristics were in agreement
with the published data. The purity of compounds was
checked by GLC on a chromatograph Tsvet-4 equipped
with a katharometer, metal column 3×3000 mm,
stationary phase 15% of Carbowax 20M on Chezasorb,
oven temperature 60°C, vaporizer temperature 150°C,
that of detector 170°C.
A fair correlation exists between the oxidation rate
of nitroethane by polyhaloalkanes and the electron
affinity of these acceptors calculated by equation (1);
the correlation is described by expression (2). This fact
additionally confirms that the electron transfer from the
nitrocarbanion to the acceptor is the limiting stage of
the process.
Nitroethane oxidation with ammonium persulfate.
To a solution of 5 g (0.066 mol) of nitroethane, 4.0 g
(0.1 mol) of sodium hydroxide, and 13.8 g (0.2 mol) of
sodium nitrite in 200 ml of water was added at 0–10°C
45.6 g (0.2 mol) of a mmonium persulfate. After stirring
for 1 h the reaction mixture was diluted to a volume of
250 ml. 10 μl of the solution obtained was injected with
a calibrated microsyringe into 6.0 ml of 0.1 N NaOH
solution, and the UV spectrum was recorded. The optical
density in the absorption maximum at 381 nm (0.29)
taking into account the molar extinction [28]
corresponded to the 1,1-dinitroethane yield 15%.
(2)
ΔG≠ = (0.09 0.01) EA(RX) – (17 1);
n 7, r 0.95, s 0.16.
Equation (2) is a typical example of fulfillment of
the extrathermodynamical relation between the kinetic
and thermodynamic parameters of electron transfer
process [25]. The slope of this line characterizes the
position of the transition state on the reaction coordinate.
Its relatively small value (0.09) reveals that the transition
state is close to the initial reagents. Inasmuch as the
reaction of polyhaloalkanes with nitrocarbanions is
exothermal these results are well consistent with the
known Hammond rule [26] stating that an early transition
state is characteristic of such reactions.
The diluted reaction mixture was extracted with ethyl
ether (3×100 ml). The ether extracts were washed with
water, 5% sodium hydrogen carbonate solution, and
dried with magnesium sulfate. The solvent was
evaporated, the residue was distilled in a vacuum. We
obtained 0.86 g (35%) of 3,4,5-trimethylisoxazole, bp
135–137°C (250 mm Hg) [29], nD20 1.456 [29]. 1H NMR
spectrum, δ, ppm: 2.20 s (3H, 5-CH3), 2.10 s (3H,
3-CH3), 1.85 s (3H, 4-CH3). Found, %: C 64.47; H 7.99;
N 12.81. M 113 (benzene). C6H9NO. Calculated, %:
C 64.84; H 8.16; N 12.60. M 111.14.
EXPERIMENTAL
1H NMR spectra were registered on a spectrometer
Perkin Elmer R-12 (60 ΜHz) from solutions in acetone-
d6, reference HMDS. IR spectra were recorded on
a spectrophotometer Specord 75IR from thin films, UV
spectra, on a spectrophotometer Perkin Elmer 402.
Molecular weights were measured by reversed
ebullioscopic method.
Oxidation of 1-nitrobutane was done similarly. By
vacuum distillation we obtained 1.3 g (25%) of 4-nitro-
4-octene, bp 67–69°C (2 mm Hg), nD20 1.4595 {66–68°C
(2 mm Hg), nD20 1.4593 [30]}. Found, %: C 61.34; H 9.47;
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 43 No. 5 2007

PETROVA et al.
650
of polyhaloalkane was added, the reaction mixture was
sampled intermittently by a calibrated microsyringe and
poured into a definite volume of 0.1 N NaOH. The
reaction progress was monitored by 1,1-dinitroethane
anion accumulation. The concentration of nitroethane
lithium salt was 0.0825 mol l−1, that of polyhaloalkane,
0.165 mol l−1 (stoichiometric ratio), sodium nitrite was
taken in excess, 0.5–1.0 mol l−1.
N 8.59. M 160 (benzene). C8H15NO2. Calculated, %:
C 61.12; H 9.62; N 8.91. M 157.21.
The mother liquor remaining after extraction was
acidified with hydrochloric acid and then treated with
excess 2,4-dinitrophenylhydrazine to obtain butyr-
aldehyde 2,4-dinitrophenylhydrazone in a quantity
corresponding to 1.4 g (30%) of butyraldehyde, mp
122°C [31], no melting point depression on mixing with
an authentic sample.
The rate constants were calculated by the known
second-order equation [33] as an arithmetic mean of three
parallel runs carried out under identical conditions. The
errors in constants determination did not exceed 5–7%.
Oxidation of 2-nitropropane was done similarly.
The reaction mixture was poured on ice, the separated
precipitate was filtered off. We obtained 1.8 g (35%) of
2,3-dimethyl-2,3-dinitrobutane, mp 210°C [17], no
melting point depression on mixing with an authentic
sample.
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