Specificity of the reaction of tetranitromethane with alkenes in nitromethane

Article abstract of DOI:10.1007/s11178-005-0333-5

Reactions of tetranitromethane with a number of di- and trisubstituted olefins in nitromethane were studied. Vinylcyclopropanes and phenylcycloalkenes reacted with tetranitromethane in an unexpected fashion, leading to formation of alkyltrinitromethanes a

Full text of DOI:10.1007/s11178-005-0333-5

Russian Journal of Organic Chemistry, Vol. 41, No. 9, 2005, pp. 1265–1270. Translated from Zhurnal Organicheskoi Khimii, Vol. 41, No. 9, 2005,
pp. 1292–1297.
Original Russian Text Copyright © 2005 by Ivanova, Averina, Budynina, Korlyukov, Antipin, Kuznetsova, Zefirov.
Specificity of the Reaction of Tetranitromethane
with Alkenes in Nitromethane
O. A. Ivanova, E. B. Averina, E. M. Budynina, A. A. Korlyukov, M. Yu. Antipin,
T. S. Kuznetsova, and N. S. Zefirov
Faculty of Chemistry, Moscow State University, Vorob’evy gory 1, Moscow, 119899 Russia
e-mail: elaver@org.chem.msu.ru
Received January 19, 2005
Abstract—Reactions of tetranitromethane with a number of di- and trisubstituted olefins in nitromethane were
studied. Vinylcyclopropanes and phenylcycloalkenes reacted with tetranitromethane in an unexpected fashion,
leading to formation of alkyltrinitromethanes and vicinal nitro alcohols.
Reactions of tetranitromethane with alkenes have
been the subject of numerous studies [1–3]. According
to published data, tetranitromethane reacts with olefins
to afford, depending on the substrate structure, 3,3-di-
nitroisoxazolidines, tetranitropropanes, nitroalkenes, or
α-nitro ketones [1]. The data on solvent effect in
reactions of tetranitromethane with alkenes are few in
number and are often contradictory. Ratsino et al. [4]
were the only to report that the reaction of tetranitro-
methane with substituted styrenes follow different path-
ways, depending on the polarity of aprotic solvent [4].
the reaction direction nor the yield of the correspond-
ing isoxazolidines.
However, solvent effect on the reactions of tetra-
nitromethane with vinylcyclopropanes and phenyl-
cycloalkenes may be considerable since the substrates
could give rise to stable carbocations [9, 10]; therefore,
unusual products may be formed, depending on the
conditions. According to our previous data [6], tetra-
nitromethane reacts with 2-cyclopropylpropene in
petroleum ether to give a mixture of isoxazolidine I
and 2-cyclopropyl-2-methyl-1,1,1,3-tetranitropropane
(II). When the same reaction was carried out in nitro-
methane, the major product was trinitro derivative III
(Scheme 1). Formalistically, compound III may be
regarded as product of addition of CH(NO2)3 to the
initial alkene. The yield of the expected adduct II did
not exceed 10%. The structure of III was unambigu-
In continuation of our recent studies on reactions of
tetranitromethane with olefins containing small rings
[5–8], in the present work we made an attempt to
examine solvent effect on these reactions. We pre-
viously showed that methylidenecyclobutane and bi-
cyclobutylidene react with tetranitromethane in such
solvents as petroleum ether and methylene chloride to
give isoxazolidine derivatives [5–8]. We also found
that the use of nitromethane as solvent changes neither
1
ously confirmed by the H and 13C NMR and mass
spectra and elemental analysis (see Experimental). It
should be noted that formation of trinitro derivatives in
Scheme 1.
O2N
O2N
O2N
NO2
Petroleum ether
+
Me
N
Me
C(NO2)3
O
O
Me
CH2
+
C(NO2)4
I, 72%
NO2
II, 10%
Me
Me
C(NO2)3
MeNO2
+
C(NO2)3
Me
Me
II, <10%
III, 46%
1070-4280/05/4109-1265 © 2005 Pleiades Publishing, Inc.

IVANOVA et al.
1266
Scheme 2.
C(NO3)2
R1
R2
·
H
R3
·
R3
R1
R1
R2
R3
R1
R2
R3
C(NO2)4
·
·
A
C(NO2)4
C(NO2)3 NO2
R2
R1
R2
R3
CTC
NO2
B
R1
R3
(O2N)3C
R1
(O2N)3C
·
·
H (Solv)
NO2
C(NO2)3
C(NO2)3
CH2R3
A
B
R1
NO2
–CH(NO2)3
R2
R2
NO2
R3
O
O
NO2
C
D
F
N
C
NO2
R1
R2
R3
R3
O
O2N
O2N
O2N
R1
R2
R3
MeNO2
NO2
O
O
R1
R2
N
N
NO2
OH
O
O2N
NO2
H
E
G
reactions of olefins with tetranitromethane was not
reported previously.
from the solvent to produce trinitroalkane C or takes
up ·NO2 thus leading to tetranitro derivative D.
The reaction of 1,1-dicyclopropylethene with tetra-
nitromethane in petroleum ether gives 2,2-dicyclo-
propyl-1,1,1,3-tetranitropropane (IV) as the only prod-
uct (yield 80%) [6]. Surprisingly, the same substrate
reacted with tetranitromethane in nitromethane to give
vicinal nitro alcohol V as the major product, though
trace amounts of adduct IV and trinitro derivative VI
were also formed (Scheme 3).
Reactions of 1-phenylcycloalkenes with tetranitro-
methane also showed an appreciable dependence on
the solvent. According to the data of [12], the products
of these reactions in petroleum ether were the corre-
sponding tetranitro derivatives. 1-Phenylcyclopentene
and 1-phenylcyclohexene reacted with tetranitro-
Scheme 2 illustrates the reaction mechanism which
was proposed on the basis of modern views on the
mechanism of tetranitromethane reactions with olefins,
including the results of our studies [8, 11]. Presumably,
tetranitromethane and olefin initially form charge-
transfer complex (CTC). Electron transfer in CTC
from the donor (olefin) to tetranitromethane gives the
corresponding radical cation, nitryl radical, and tri-
nitromethyl anion. Recombination of the radical–ion
pair (vinylcyclopropane radical cation and trinitro-
methyl anion) leads to radical A. The regioselectivity
of this process is controlled by strong electron density
deficit on the internal carbon atom in substituted vinyl-
cyclopropane. Primary radical A abstracts hydrogen
Scheme 3.
NO2
NO2
Me
C(NO2)4, MeNO2
+
+
CH2
C(NO2)3
OH
C(NO2)3
IV, 5%
V, 45%
VI, 5%
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 41 No. 9 2005

SPECIFICITY OF THE REACTION OF TETRANITROMETHANE WITH ALKENES
1267
Scheme 4.
NO2
3'
4'
5'
2'
1'
Ph
OH
Ph
Ph
6'
C(NO2)4, MeNO2
O
+
+
Ph
HO
3
5
NO2
NO2
2
6
( )n
( )n
( )n
1
4
Ph
VIIa, VIIb
VIIIa, VIIIb
IX, <5%
VII, n = 1, yield 40% (a); n = 2, 41% (b); VIII, n = 1, 26% (a); n = 2, 33% (b).
methane in nitromethane to afford vicinal nitro al-
cohols VIIa and VIIb, as well as nitroalkenes VIIIa
and VIIIb, respectively. In addition, a small amount of
ether IX was isolated in the reaction of 1-phenylcyclo-
hexene with tetranitromethane (Scheme 4).
duce this procedure and failed to isolate the corre-
sponding product as individual substance. The reaction
resulted in formation of a complex mixture of products
which were difficult to separate, and isoxazolidine
derivative was detected among the products.
According to the NMR data, compounds VIIa and
VIIb were formed as a single diastereoisomer, assum-
ingly with trans orientation of the hydroxy and nitro
Thus the different behavior of the examined alkenes
in reaction with tetranitromethane in nitromethane
originates from the existence of two possible paths of
recombination of intermediate species (olefin radical
cation, trinitromethyl anion, and nitryl radical), i.e.,
collapse of ion or radical pair. The olefins react with
tetranitromethane differently in petroleum ether and
nitromethane due to competing nucleophilic attack by
ambident trinitromethyl anion on intermediate nitro-
substituted carbocation (C- and O-alkylation), leading
1
groups. The H and 13C NMR spectra of trans-nitro
alcohol synthesized from 2-nitrocyclohexanone and
PhMgBr [13] fully coincided with those of compound
VIIb. Nitro alcohols V, VIIa, and VIIb were iden-
tified via conversion into stable tetrahydropyranyl
derivatives Xa–Xc. The structure of cyclohexanol IX
was unambiguously proved by the X-ray diffraction
data (see figure). The NO2 and RO groups, as well as
RO and OH, are arranged trans with respect to each
other. The mechanism of formation of compound IX
still remains unclear, and no published analogies of
such transformation were found.
C15'
C16'
C14'
O1'
O2'
C13'
C12'
N1
Analysis of the structure of products V and VII–IX
suggests that the first reaction stage involves recom-
bination of nitryl radical with the radical cation derived
from olefin to give nitro-substituted carbocation B.
Obviously, vicinal nitro alcohols V, VIIa, and VIIb
are formed via predominant O-alkylation of cation B
with trinitromethyl anion, followed by solvolysis of
unstable nitronate E (Scheme 2). The formation of
appreciable amounts of nitro alkenes F from phenyl-
cycloalkenes is explained by preferential stabilization
of nitro carbocation B via elimination of proton.
An analogous behavior was described previously for
some olefins having bulky substituents [14]. In the
reaction of tetranitromethane with sterically unhinder-
ed alkenes, [2+3]-cycloaddition of nitronate E to the
substrate leads to isoxazolidine derivatives H [1–8].
C11'
C2'
C1'
C6'
C4'
C3'
C5'
O
C3
C2
C4
O1
C1
C12
C5
C11
C16
C6
C15
C13
C14
According to the data of [4], the major product of
the reaction of α-methylstyrene with tetranitromethane
in nitromethane is (1-methyl-2,2,2-trinitro-1-nitro-
methylethyl)benzene. We made an attempt to repro-
Structure of the molecule of 2-(2-nitro-1-phenylcyclohexyl-
oxy)-1-phenylcyclohexanol (IX) according to the X-ray dif-
fraction data.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 41 No. 9 2005

IVANOVA et al.
1268
to tetranitropropanes and vicinal nitro alcohols, respec-
tively. Presumably, nitromethane (as more polar sol-
vent) stabilizes more polar form of trinitromethyl
anion, favoring addition of the latter at the oxygen
atom.
Reaction of olefins with tetranitromethane
(general procedure). A solution of 2.5 mol of tetra-
nitromethane in 2 ml of nitromethane was cooled to
0°C, and a solution of 2.5 mmol of the corresponding
olefin in 2 ml of nitromethane was added dropwise
under stirring. The mixture was kept for 3 days at
room temperature, the solvent was distilled off, and the
residue was subjected to column chromatography.
To conclude, it should be noted that the examined
reactions of tetranitromethane with olefins in nitro-
methane open new prospects in the synthesis of such
difficultly accessible but promising compounds as
alkyltrinitromethanes and vicinal nitro alcohols in
which the hydroxy group is attached to a tertiary
carbon atom.
2-Cyclopropyl-2-methyl-1,1,1-trinitropropane
(III). Yield 46%, Rf 0.6 (CHCl3). 1H NMR spectrum, δ,
ppm: 0.47 m (2H, cyclorpopane), 0.60 m (2H, cyclo-
propane), 1.35 s (6H, CH3), 1.64 m (1H, CH, cyclo-
propane). 13C NMR spectrum, δC, ppm(1JCH, Hz): 2.20
(CH2, cyclopropane, J = 163), 17.51 (CH, cyclopro-
pane, J = 163), 22.22 (CH3, J = 130), 44.57 (C),
136.60 [C(NO2)3]. Mass spectrum, m/z, (Irel, %): 233
(1) [M]+, 203 (35) [M – NO], 121 (51), 109 (35), 95
(34), 93 (37), 83 (100) [M – C(NO2)3], 69 (45), 55
(71). Found, %: C 36.37; H 4.93. C7H11N3O6. Calcu-
lated, %: C 36.05; H 4.72.
EXPERIMENTAL
1
The H and 13C NMR spectra were recorded on
Varian VXR-400 (400 and 100 MHz, respectively) and
Bruker DPX-300 spectrometers (300 and 75 MHz,
respectively); chloroform-d was used as solvent and
internal reference (δ 7.24, δC 77.10 ppm). The mass
spectra (electron impact, 70 eV) were obtained on
a Varian MAT-311A instrument.
1,1-Dicyclopropyl-3-nitro-2-propanol (V). Yield
1
45%, Rf 0.4 (CHCl3). H NMR spectrum, δ, ppm:
0.33–0.57 m (8H, CH2, cyclopropane), 0.88 m (2H,
CH, cyclopropane), 4.54 s (2H, CH2). 13C NMR spec-
trum, δC, ppm (1JCH, Hz): –0.75 (CH2, cyclopropane,
J = 163), 0.37 (CH2, cyclopropane, J = 162), 17.14
(CH, cyclopropane, J = 156), 70.20 (C), 85.09 (CH2,
J = 128). Mass spectrum, m/z (Irel, %): 154 (38) [M –
OH], 111 (100) [M – CH2NO2], 107 (31), 93 (10), 79
(12). Found, %: C 56.51; H 8.02; N 7.15. C8H13NO3.
Calculated, %: C 56.13; H 7.65; N 8.18.
Tetranitromethane was prepared from acetic anhy-
dride and concentrated nitric acid (d420 = 1.5 g/cm3)
according to the procedure described in [15]. 2-Cyclo-
propylpropene [16] and 1,1-dicyclopropylethene [17]
were synthesized by known methods. 1-Phenylcyclo-
hexene, 1-phenylcyclopentene, and α-methylstyrene
were commercial products.
X-Ray analysis of a single crystal of compound IX
was performed on a Siemens P3/PC diffractometer
[λ(MoKα) = 0.71073 Å, θ/2θ-scanning, 2θ < 56°].
Monoclinic crystals with the following unit cell param-
eters: a = 10.907(2), b = 10.736(2), c = 17.937(4) Å;
β = 91.36(3)°; Z = 4; V = 2099.9(7) Å3; space group
P21/n; dcalc = 1.251 g/cm3; μ = 0.85 cm–1; F(000) =
848; M 395.48. Intensities of 5358 reflections were
measured at room temperature; 5101 independent
reflections (Rint = 0.0204) were used in subsequent
refinement. The structure was solved by the direct
method and was refined with respect to F2 by the least-
squares procedure in full-matrix isotropic–anisotropic
approximation. Hydrogen atoms were localized from
the Fourier difference series of electron density, and
their positions were refined in isotropic approximation.
The final divergence factors were R1 = 0.0441 [from
3916 reflections with I > 2σ(I)] and wR2 = 0.1312 (all
reflections); GOF = 1.059. All calculations were per-
formed using SHELXTL V5.10 software package [18].
Additional information is available from the authors.
2-Nitro-1-phenylcyclopentanol (VIIa). Yield
1
40%, Rf 0.3 (CHCl3). H NMR spectrum, δ, ppm
(J, Hz): 2.01–2.86 m (6H, CH2), 5.06 d.d.d (1H,
CHNO2, 3J = 3.5, 7.7, 4J = 1.1), 7.29–7.50 m (5H, Ph).
13C NMR spectrum, δC, ppm (1JCH, Hz): 21.95 (CH2,
J = 132), 30.09 (CH2, J = 133), 36.67 (CH2, J = 132),
88.63 (C), 96.07 (CHNO2, J = 156), 126.20 (2CH, Ph),
128.52 (2CH, Ph), 128.72 (CH, Ph), 139.86 (C, Ph).
Mass spectrum, m/z (Irel, %): 261 (21) [M – NO2], 143
(2) [M – NO2 – H2O], 105 (100), 77 (38), 51 (15).
Found, %: C 64.59; H 6.67. C11H13NO3. Calculated, %:
C 63.76; H 6.32.
2-Nitro-1-phenylcyclohexanol (VIIb) [13]. Yield
41%, mp 93–94°C; published data [16]: mp 93°C;
1
Rf 0.3 (CHCl3). H NMR spectrum, δ, ppm (J, Hz):
1.55–3.10 m (8H, CH2), 4.85 t (1H, CHNO2, J = 5.0),
7.26–7.52 m (5H, Ph). 13C NMR spectrum, δC, ppm:
20.56 (CH2), 20.60 (CH2), 27.45 (CH2), 34.09 (CH2),
73.08 (C), 90.43 (CHNO2), 125.85 (2CH, Ph), 128.13
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 41 No. 9 2005

SPECIFICITY OF THE REACTION OF TETRANITROMETHANE WITH ALKENES
1269
(CH, Ph), 128.44 (2CH, Ph), 143.21 (C, Ph). Mass
spectrum, m/z (Irel, %): 221 (1) [M]+, 204 (2) [M –
OH], 186 (9), 175 (8) [M – NO2], 174 (20) [M –
HNO2], 173 (25), 145 (15), 133 (21), 105 (100), 98
(25), 91 (46), 83 (24), 77 (51), 70 (30), 55 (24). Found,
%: C 65.29; H 7.67; N 6.16. C12H15NO3. Calculated,
%: C 65.14; H 6.83; N 6.33.
63.01 (CH2O), 84.08 (CH2NO2), 90.01 (C), 94.71
(CH). Mass spectrum, m/z (Irel, %): 195 (1) [M –
CH2NO2], 154 (18) [M – C5H9O2], 111 (16), 85 (100)
(C5H9O), 41 (15) (cyclopropyl).
2-(2-Nitro-1-phenylcyclopentyloxy)tetrahydro-
2H-pyran (Xb). Yield 73%, Rf 0.5 (petroleum ether–
1
ethyl acetate, 4:1). H NMR spectrum, δ, ppm (a mix-
(5-Nitro-1-cyclopentenyl)benzene (VIIIa) [19].
ture of two diastereoisomers, A and B, at a ratio of
8:3): 1.32–2.53 m (12H + 12H, A, B), 3.19 m (1H,
CH2O, B), 3.48 m (1H, CH2O, A), 3.69 m (1H, CH2O,
B), 3.90 m (1H, CH2O, A), 4.35 m (1H, CHNO2, A),
4.48 m (1H, CHNO2, B), 5.15 m (1H, CH, A), 5.56 m
(1H, CH, B), 7.26–7.51 m (5H + 5H, Ph, A, B).
13C NMR spectrum, δC, ppm (A+B): 20.09 (CH2, A),
20.20 (CH2, B), 22.03 (CH2, B), 22.23 (CH2, A), 25.17
(CH2, B), 25.27 (CH2, A), 25.55 (CH2, B), 30.49 (CH2,
A), 30.79 (CH2, B), 30.85 (CH2, A), 31.85 (CH2, A),
32.10 (CH2, B), 63.48 (CH2O, B), 63.84 (CH2O, A),
91.54 (C, B), 92.69 (C, A), 94.15 (CHNO2, A), 94.90
(CHNO2, B), 95.90 (CH, A), 96.36 (CH, B), 127.98
(2CH, Ph), 128.06 (2CH, Ph), 128.12 (2CH, Ph),
128.39 (2CH, Ph), 128.75 (CH, Ph), 128.79 (CH, Ph),
135.06 (C, Ph), 137.12 (C, Ph). Found, %: C 66.01;
H 7.79; N 4.81. C16H21NO4. Calculated, %: C 65.98;
H 7.27; N 4.81.
1
Yield 26%, Rf 0.7 (CHCl3). H NMR spectrum, δ,
ppm: 2.01–3.05 m (4H, CH2), 5.96 m (1H, CH),
6.70 m (1H, CH), 7.29–7.50 m (5H, Ph). 13C NMR
spectrum, δC, ppm: 31.45 (CH2), 32.15 (CH2), 92.48
(CHNO2), 125.85 (2CH, Ph), 128.39 (CH, Ph), 129.31
(2CH, Ph), 133.13 (C), 136.72 (CH=), 138.72 (C).
(6-Nitro-1-cyclohexenyl)benzene (VIIIb) [20].
Yield 33%, mp 36°C; published data [18]: mp 36–
1
37°C; Rf 0.8 (CHCl3). H NMR spectrum, δ, ppm
(J, Hz): 1.68–2.50 m (6H, CH2), 5.56 m (1H, CHNO2),
3
6.42 d.d (1H, CH=, J = 3.6, 4.4), 7.31 m (5H, Ph).
13C NMR spectrum, δC, ppm: 17.51 (CH2), 25.63
(CH2), 29.19 (CH2), 83.24 (CHNO2), 125.70 (2CH,
Ph), 128.20 (CH, Ph), 128.88 (2CH, Ph), 131.49 (C),
134.08 (CH=), 139.02 (C).
(1RS,2RS,1'SR,2'RS)-2-(2-Nitro-1-phenylcyclo-
hexyloxy)-1-phenylcyclohexanol (IX). Yield 4%,
1
mp 194–195°C. H NMR spectrum, δ, ppm (J, Hz):
2-(2-Nitro-1-phenylcyclohexyloxy)tetrahydro-
1.00–2.00 m (15H, cyclohexane), 2.76 d.d.d (1H,
cyclohexane, J = 4.7, 14.5, 14.1), 3.89 m (1H, CHO),
4.70 m (1H, CHNO2), 7.27–7.52 m (10H, Ph), 10.13
(1H, OH).
2H-pyran (Xc). Yield 86%, Rf 0.6 (petroleum ether–
ethyl acetate, 4:1). H NMR spectrum, δ, ppm (a mix-
1
ture of two diastereoisomers, A and B, at a ratio of
3:1): 1.30–2.90 m (14H + 14H, A, B), 3.41 m (1H,
CH2O, A), 3.75 m (1H, CH2O, B), 3.90 m (1H, CH2O,
B), 3.98 m (1H, CH2O, A), 4.22 m (1H, CHNO2, A),
4.33 m (1H, CHNO2, B), 5.04 m (1H, CH, A), 5.32 m
(1H, CH, B), 7.23–7.55 m (5H + 5H, Ph, A, B).
13C NMR spectrum, δC, ppm (A+B): 19.32 (CH2, A),
19.43 (CH2, B), 20.40 (CH2, A), 20.46 (CH2, A), 20.56
(CH2, B), 20.77 (CH2, B), 25.24 (CH2, B), 25.35 (CH2,
A), 27.40 (CH2, A), 27.58 (CH2, A), 27.78 (CH2, A),
28.61 (CH2, B), 32.05 (CH2, A), 32.37 (CH2, B), 63.81
(CH2O, B), 64.25 (CH2O, A), 78.44 (C, A, B), 88.86
(CHNO2, B), 90.21 (CHNO2, A), 94.82 (CH, B), 95.55
(CH, A), 127.22 (2CH, Ph), 127.33 (2CH, Ph),
128.15 (2CH, Ph, A, B), 128.54 (2CH, Ph), 128.63
(2CH, Ph), 140.60 (2C, Ph). Found, %: C 67.31;
H 7.87; N 4.68. C17H23NO4. Calculated, %: C 66.86;
H 7.59; N 4.59.
Tetrahydropyranyl derivatives of alcohols V,
VIIa, and VIIb (general procedure). Alcohol V, VIIa,
or VIIb, 2 mmol, was added to a solution of 3 mmol of
dihydropyran and 0.01 mmol of pyridinium p-toluene-
sulfonate in 7 ml of methylene chloride. The mixture
was stirred for 4 h and left overnight. It was then
washed with a saturated aqueous solution of sodium
chloride (2×3 ml) and evaporated, and the product was
isolated from the residue by column chromatography.
2-(1,1-Dicyclopropyl-2-nitroethoxy)tetrahydro-
2H-pyran (Xa). Yield 76%, Rf 0.7 (petroleum ether–
1
ethyl acetate, 4:1). H NMR spectrum, δ, ppm (J, Hz):
0.03–1.93 m (16H), 3.51 m (1H, CH2O), 4.87 m (1H,
2
CH2O), 4.61 d (1H, CH2NO2, J = 10.2,), 4.76 d (1H,
CH2NO2, 2J = 10.2), 4.99 m (1H, CH). 13C NMR spec-
trum, δC, ppm: –0.99 (CH2, cyclopropyl), 1.12 (CH2,
cyclopropyl), 1.45 (CH2, cyclopropyl), 2.56 (CH2,
cyclopropyl), 13.66 (CH, cyclopropyl), 14.55 (CH,
cyclopropyl), 19.75 (CH2), 25.58 (CH2), 30.80 (CH2),
This study was performed under financial support
by the Russian Foundation for Basic Research (project
no. 00-15-97359).
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 41 No. 9 2005

IVANOVA et al.
10. Wiberg, K.B., and Ashe, A.J., III, J. Am. Chem. Soc.,
1270
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