Reaction of 2-methyl-3-morpholino-1-phenylprop-2-en-1-one with Ru 3(CO)12

Article abstract of DOI:10.1007/s11172-006-0565-8

The reaction of Ru₃(CO)₁₂ with 2-methyl-3-morpholino- 1-phenylprop-2-en-1-one (1) produced the Ru₆(CO)₁₆(μ ₄-η¹:η¹:η²: η²-PhC(O)-C(Me)=C)₂ (2), R

Full text of DOI:10.1007/s11172-006-0565-8

Russian Chemical Bulletin, International Edition, Vol. 55, No. 12, pp. 2143—2148, December, 2006
2143
Reaction of 2ꢀmethylꢀ3ꢀmorpholinoꢀ1ꢀphenylpropꢀ2ꢀenꢀ1ꢀone
with Ru3(CO)12
N. A. Shtel´tser,ꢀ S. V. Osintseva, P. V. Petrovskii, A. Z. Kreindlin, and F. M. Dolgushin
A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences,
28 ul. Vavilova, 119991 Moscow, Russian Federation.
Fax: +7 (495) 135 5085. Eꢀmail: CBETA@ineos.ac.ru
The reaction of Ru3(CO)12 with 2ꢀmethylꢀ3ꢀmorpholinoꢀ1ꢀphenylpropꢀ2ꢀenꢀ1ꢀone (1)
1
1
2
2
3
produced the Ru6(CO)16(µ ꢀη :η :η :η ꢀPhC(O)—C(Me)=C)2 (2), Ru2O2(CO)4(η ꢀ
4
OC(Ph)C(Me)C(H)C(Me)2C(Ph))2 (3), and [Ru(CO)2(PhCO2)(O(CH2—CH2)2NH]2 (4)
complexes, which were characterized by IR and NMR spectroscopy. The structures of the
complexes were established by Xꢀray diffraction. The formation of the complexes is accompaꢀ
nied by deamination of ligand 1. Complexes 2 and 3 bearing the vinyl ketone groups contain
fiveꢀmembered oxaruthenacycles and dihydropyran rings. Morpholine is not removed from the
reaction mixture and leads to the formation of complex 4.
3
Key words: dodecacarbonyltriruthenium, oxaruthenacycles, η ꢀdihydropyran rings, carbꢀ
oxylate rings, Xꢀray diffraction study, IR spectroscopy, NMR spectroscopy.
Earlier,1 we have demonstrated that most of the comꢀ
plexes prepared by the reactions of Ru3(CO)12 with
oxadienes (α,βꢀunsaturated ketones) contain the same
structural fragments, viz., fiveꢀmembered oxaruthenaꢀ
cycles and dihydropyran rings, involved in πꢀcoordinaꢀ
tion to metal atoms. The variation of substituents at the
carbonyl group of oxadiene (aryls, alkyls, or amino groups)
did not lead to new structural types. When a secondary
amino group was attached to the Cβ atom of the olefin
fragment of oxadiene, the reaction with Ru3(CO)12 proꢀ
duced complexes with sixꢀmembered azaoxaruthenaꢀ
cycles2 due to the appearance of an additional reaction
center (active N—H bond of the secondary amino group).
It was of interest to elucidate how the replacement of the
secondary amino group in the β position of the olefin
fragment of oxadiene by the tertiary amino group influꢀ
ences the structure of the resulting complexes. Earlier,3 it
has been demonstrated that βꢀaminovinyl ketones do not
react with iron carbonyls. Other examples of the reactions
of these ketones with ironꢀgroup metal carbonyls are lackꢀ
ing in the literature.4,5 In the present study, we examined
the reaction of Ru3(CO)12 with 2ꢀmethylꢀ3ꢀmorpholinoꢀ
1ꢀphenylpropꢀ2ꢀenꢀ1ꢀone (1).
thenium complexes 2, 3, and 4 (Scheme 1) were isolated
by chromatography in 4, 18, and 25% yields, respectively.
The structures of complexes 2—4 were established by
Xꢀray diffraction. In the crystals structure, hexanuclear
complex 2 (Fig. 1, Table 1) occupies a special position
on the twofold axis passing through the Ru(3) and
Ru(4) atoms. The metal core looks like a twisted
ladder consisting of two quadrangles fused at the
Ru(3)—Ru(4) bond (Ru(1)—Ru(2)—Ru(3)—Ru(4) and
Ru(1A)—Ru(2A)—Ru(3)—Ru(4)), each quadrangle beꢀ
ing nonplanar. In complex 2, there are seven Ru—Ru
bonding distances in the range of 2.633(1)—2.9175(7) Å
with the shortest distance between the Ru(3) and Ru(4)
atoms. The formation of complex 2 is accompanied by
elimination of the morpholine fragment from the starting
ligand. The oxadiene fragments chelate the Ru atoms to
form fiveꢀmembered oxaruthenacycles, which are involved
in πꢀcoordination to the Ru(2) and Ru(2A) atoms. Earꢀ
lier, we have observed the formation of structurally simiꢀ
lar oxaruthenacycles in the reactions of Ru3(CO)12 with
oxadiene ligands.1,6 The oxaruthenacycles in complex 2
are distinguished mainly by the unusual µ4 coordination
of the C(11) atom (four Ru—C(11) distances are in
the range 2.052(6)—2.234(6) Å). Apparently, this acꢀ
counts for a slight nonplanarity of the oxadiene system
(O(9)—C(9)—C(10)—C(11) torsion angle is 15.7°).
The analogous hexanuclear cluster Ru6(CO)16(µ4ꢀ
η1:η1:η2:η2ꢀCC(H)C(O)Me)2 was synthesized by the reꢀ
action of Ru3(CO)12 with butꢀ3ꢀynꢀ2ꢀol.7 In spite of the
difference in the nature of substituents at the C atoms of
oxaruthenacycles, the structure of this cluster is comꢀ
Results and Discussion
The reaction of Ru3(CO)12 with compound 1 was carꢀ
ried out under reflux in heptane for 8 h. The course of the
reaction was monitored by changes in the IR spectra in
the metal carbonyl stretching region. The reaction afꢀ
forded a mixture of products, from which three new ruꢀ
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2063—2068, December, 2006.
1066ꢀ5285/06/5512ꢀ2143 © 2006 Springer Science+Business Media, Inc.

2144
Russ.Chem.Bull., Int.Ed., Vol. 55, No. 12, December, 2006
Shtel´tser et al.
Scheme 1
pletely identical to that of complex 2. It was hypothesized7
that butꢀ3ꢀynꢀ2ꢀol is oxidized to the corresponding keꢀ
tone in one of the reaction steps. Therefore, the mechaꢀ
nism of formation of complex 2 may be analogous to that
for the complex described in the study.7
Centrosymmetric complex 3 (Fig. 2, Table 2) consists
of two sixꢀmembered dihydropyran rings involved in
η3ꢀcoordination to the Ru atoms. The Ru atoms are linked
to each other by the bridging O atoms to form the fourꢀ
membered Ru2O2 ring. Earlier, we have synthesized strucꢀ
turally similar complexes by the reactions of Ru3(CO)12
with 4ꢀphenylbutꢀ3ꢀenꢀ2ꢀone6 and 1ꢀpꢀtolylꢀ3ꢀphenylꢀ
propꢀ2ꢀenꢀ1ꢀone.1 In spite of the presence of different
substituents in the starting ligands, all the compounds
synthesized contain dihydropyran rings with similar strucꢀ
tures.1,6
The formation of complex 3, like the synthesis of comꢀ
plex 2, is accompanied by elimination of the morpholine
fragment from the starting ligand. The oxadiene system of
ligand 1, apparently, behaves analogously to oxadienes,
which we have studied earlier.1,6 It forms oxaruthenaꢀ
cycles, which are transformed into the dihydropyran rings
in the presence of excess ligand (Scheme 2). Most probꢀ
ably, it is impossible to prepare complexes 2 and 3 from
the corresponding oxadiene (2ꢀmethylꢀ1ꢀphenylpropꢀ
2ꢀenꢀ1ꢀone) by the direct reaction with Ru3(CO)12, beꢀ
O(5)
O(7)
C(5)
O(4)
C(4)
C(7)
Ru(2A)
Ru(3)
Ru(2)
C(6)
O(6)
C(11)
C(18)
C(10)
O(3)
C(13)
C(1)
C(14)
C(9)
O(1)
Ru(1)
Ru(1A)
C(12)
Ru(4)
C(8)
O(9)
C(15)
C(14)
C(17)
O(8)
C(16)
C(14)
Fig. 1. Molecular structure of complex 2.

Reactions of Ru3(CO)12
Russ.Chem.Bull., Int.Ed., Vol. 55, No. 12, December, 2006 2145
Table 1. Selected bond lengths (d) and bond
angles (ω) in complex 2
C(11)
C(12)
C(10)
C(13)
Parameter
Value
Bond
Ru(1)—Ru(2)
Ru(1)—Ru(4)
Ru(1)—O(9)
Ru(1)—C(11)
Ru(2)—Ru(3)
Ru(2)—C(10)
Ru(2)—C(11)
Ru(3)—Ru(4)
Ru(3)—C(11)
Ru(4)—C(11)
O(9)—C(9)
C(9)—C(10)
C(10)—C(11)
Angle
d/Å
C(9)
C(8)
2.7668(8)
2.8052(6)
2.106(4)
2.234(6)
2.9175(7)
2.220(6)
2.130(6)
2.6332(10)
2.111(6)
2.052(6)
1.256(7)
1.451(8)
1.466(9)
ω/deg
C(15)
C(3)
Ru(1A)
O(3)
C(14)
C(4)
C(5)
O(1)
O(4)
C(1)
C(6)
O(3A)
C(7)
C(22)
C(17)
C(2)
C(16)
O(2)
C(18)
Ru(2)—Ru(1)—Ru(4)
Ru(1)—Ru(2)—Ru(3)
Ru(4)—Ru(3)—Ru(2)
Ru(2)—Ru(3)—Ru(2A)*
Ru(3)—Ru(4)—Ru(1)
Ru(1)—Ru(4)—Ru(1A)*
O(9)—Ru(1)—C(11)
C(9)—O(9)—Ru(1)
O(9)—C(9)—C(10)
C(9)—C(10)—C(11)
C(10)—C(11)—Ru(1)
92.09(2)
80.80(2)
92.41(2)
175.18(3)
85.28(2)
170.56(3)
76.6(2)
115.8(4)
120.0(6)
113.3(5)
105.3(4)
C(21)
C(20)
C(19)
Fig. 2. Molecular structure of complex 3.
Table 2. Selected bond lengths (d) and bond
angles (ω) in complex 3
Parameter
Value
Bond
Ru(1)—O(3)
Ru(1)—O(3)*
Ru(1)—C(5)
Ru(1)—C(6)
Ru(1)—C(7)
O(3)—C(3)
O(4)—C(3)
O(4)—C(7)
C(3)—C(4)
C(4)—C(5)
C(5)—C(6)
C(6)—C(7)
d/Å
2.086(1)
2.189(1)
2.148(2)
2.245(2)
2.449(2)
1.391(2)
1.456(2)
1.397(2)
1.559(3)
1.525(3)
1.430(3)
1.396(3)
ω/deg
* The atom labeled with the suffix A is related to
the unlabeled atom by the symmetry operation
–x, y, –z + 1/2.
cause vinyl ketones containing only H atoms in the
β position are known8,9 to be able to undergo polymerꢀ
ization.
Scheme 2
Angle
O(3)—Ru(1)—O(3A)*
Ru(1)—O(3)—Ru(1A)*
C(3)—O(3)—Ru(1)
C(3)—O(3)—Ru(1A)*
C(7)—O(4)—C(3)
O(3)—C(3)—O(4)
O(3)—C(3)—C(4)
O(4)—C(3)—C(4)
C(5)—C(4)—C(3)
C(6)—C(5)—C(4)
C(7)—C(6)—C(5)
C(6)—C(7)—O(4)
78.60(6)
101.40(6)
106.9(1)
125.0(1)
115.1(2)
107.3(2)
107.8(2)
108.9(2)
105.7(2)
118.2(2)
115.8(2)
120.0(2)
In complex 4 (Fig. 3, Table 3), two Ru atoms are
linked by two benzoate bridges. Each Ru atom is addiꢀ
tionally coordinated by two carbonyl groups and the lone
* The atom labeled with the suffix A is related to
the unlabeled atom by the symmetry operation
–x, –y + 1, –z.

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Russ.Chem.Bull., Int.Ed., Vol. 55, No. 12, December, 2006
Shtel´tser et al.
tion of carboxylic acids with Ru3(CO)12 in the presence of
amines.10,11 Morpholine generated by deamination of the
ligand is not removed from the reaction mixture, thus
resulting in the formation of complex 4.
C(7)
C(6)
C(8)
The IR and NMR spectroscopic data for complexes
2—4 are in complete agreement with the Xꢀray diffraction
data. The IR spectrum of complex 2 shows eight bands
with different intensities in the metal carbonyl stretching
region, which is consistent with the C2 symmetry of the
molecule in the crystal; ν(CO)/cm–1 (hexane): 2068 s,
2056 s, 2048 m, 2032 m, 2024 m, 2010 m, 1998 w, 1958 w.
C(5)
C(3)
C(9)
C(4)
O(3)
O(4)
C(12)
C(13)
N(2)
N(1)
Ru(2)
Ru(1)
C(15)
1
The H NMR spectrum of complex 2 has one set of sigꢀ
O(5)
C(11) C(10)
O(6)
nals for the protons of two equivalent oxaruthenacycles;
δ: 2.69 (s, 3 H, Me); 7.27—7.70 (m, 5 H, Ph).
C(14)
C(2)
C(1)
O(1)
The IR spectrum of complex 3 shows two wellꢀreꢀ
solved bands with equal intensities in the metal carbonyl
stretching region, which is indicative of cis positions of
two CO ligands and is consistent with the centrosymmetꢀ
ric structure of the complex; ν(CO)/cm–1 (hexane):
2026 s, 1958 s. The equivalence of two dihydropyran
O(2)
Fig. 3. Molecular structure of complex 4.
Table 3. Selected bond lengths (d) and bond
angles (ω) in complex 4
1
ligands in complex 3 is confirmed by H NMR spectroꢀ
1
scopy. The H NMR spectrum has one set of signals for
Parameter
Value
the protons of the dihydropyran ligands; δ: 0.68, 0.76,
and 1.89 (all s, 3 H each, Me); 2.79 (s, H, CH); 7.30—7.89
(m, 10 H, 2 Ph).
Bond
d/Å
Ru(1)—Ru(2)
Ru(1)—C(1)
Ru(1)—O(3)
Ru(1)—N(1)
Ru(2)—C(2)
Ru(2)—O(4)
Ru(2)—N(2)
Angle
2.663(2)
1.827(14)
2.116(8)
2.158(17)
1.86(2)
2.108(8)
2.25(2)
ω/deg
The IR spectrum of complex 4 shows two strong and
one weak bands in the metal carbonyl stretching region
(ν(CO)/cm–1 (hexane): 2030 v.s, 1980 w, 1950 s). Similar
IR spectroscopic data for related complexes were pubꢀ
lished in the studies.10—12 The presence of three bands in
the IR spectrum of complex 4 can be a consequence of a
lowering of the molecular symmetry due to disorder of the
amine ligands at the Ru atoms. The 1H NMR spectrum of
complex 4 has one set of signals for the protons of two
morpholine and two carboxylate ligands; δ: 2.91 (br.s,
1 H, NH); 3.40 (q, 4 H, CH2O); 3.81 and 4.10 (both dt,
2 H each, СH2N); 7.30—7.83 (m, 5 H, Ph). The 1H NMR
spectrum provides evidence for the nonequivalence of the
protons of each CH2 group bound to the N atoms. The
N(1)—Ru(1)—Ru(2)
N(2)—Ru(2)—Ru(1)
161.6(5)
156.6(7)
electron pair of the N atom of the morpholine molecule.
A large number of related ruthenium complexes with difꢀ
ferent nitrogenꢀcontaining ligands (pyridine, acetonitrile,
pyrazole, etc.) and carboxylate bridges (acetate, pivalate,
propionate, etc.) were described in the literature.* In all
these complexes, the N atoms are sp2ꢀhybridized (pyriꢀ
dine and its derivatives) or spꢀhybridized (acetonitrile).
Complex 4 is the only complex containing the sp3ꢀhyꢀ
bridized N atoms. The Ru—Ru (2.663(2) Å) and Ru—N
(2.16(2) and 2.25(2) Å) distances in complex 4 are simiꢀ
lar to those observed in structurally related complexes
(Ru—Ru and Ru—N, 2.672—2.712 and 2.16—2.27 Å,
respectively). In the crystal structure, complex 4 occupies
a special position on the mirror plane passing through the
Ru(1), Ru(2), N(1), and O(5) atoms. One of the morphoꢀ
line ligands is disordered over two positions. The possible
route to the synthesis of complexes analogous to comꢀ
plex 4 has been described earlier in the study of the reacꢀ
1
presence of the amine proton observed in the H NMR
spectrum of complex 4 confirms that deamination of
ligand 1 leads to the formation of morpholine.
It is known that tertiary amines in reactions with ironꢀ
group metal carbonyls undergo a series of transformaꢀ
tions: the C—N bond cleavage, activation of αꢀ and
βꢀaliphatic and aromatic C—H bonds, and decarboꢀ
nylation of one of the metal carbonyl CO groups.4,13 The
C—N bond cleavage was observed also in the reactions of
Ru3(CO)12 with alkyneamines.14,15 In the present study,
we demonstrated that similar processes occur with terꢀ
tiary βꢀaminovinyl ketone.
In the reaction with Ru3(CO)12, 2ꢀmethylꢀ3ꢀmorphoꢀ
linoꢀ1ꢀphenylpropꢀ2ꢀenꢀ1ꢀone undergoes the following
transformations: 1) coordination of the metal atom at the
oxadiene fragment is accompanied by deamination with
* Cambridge Structural Database, May 2005.

Reactions of Ru3(CO)12
Russ.Chem.Bull., Int.Ed., Vol. 55, No. 12, December, 2006 2147
1
1
2
2
ruthenium Ru6(CO)16(µ ꢀη :η :η :η ꢀPhC(O)—C(Me)=C)2 (2),
the result that complexes 2 and 3 do not contain morphoꢀ
line; 2) coordination of the metal atom at the amine fragꢀ
ment leads to activation of the C—H bonds resulting in
the appearance of additional H atoms necessary for the
formation of complex 3; 3) coordination of amine at one
of the metal carbonyl groups leads to decarbonylation of
the complex. In our opinion, the CO group serves as a
source of oxygen for the formation of the benzoate fragꢀ
ment in complex 4.
Therefore, the replacement of the secondary amino
group at the Cβ atom of oxadiene2 with the tertiary amino
group results in the fragmentation of aminovinyl ketone
in the reaction with Ru3(CO)12. The amine and vinyl
ketone groups of the ligand are present in different reacꢀ
tion products.
4
3
di{µ ꢀ[4, 5, 6ꢀη ꢀ5ꢀmethylꢀ3ꢀdimethylꢀ2, 6ꢀdiphenylꢀ
3,4ꢀdihydropyranꢀ2ꢀyl]oxo}bis(dicarbonylruthenium)
Ru2O2(CO)4(η ꢀOC(Ph)C(Me)C(H)C(Me)2C(Ph))2 (3), and
3
di(µꢀbenzoato)tetracarbonylꢀbis(morpholine)diruthenium
[Ru(CO)2(PhCO2)(O(CH2—CH2)2NH]2 (4). A mixture of
Ru3(CO)12 (320 mg, 0.5 mmol) and compound 1 (231 mg,
1 mmol) in heptane (150 mL) was refluxed for 8 h and then
concentrated. The residue was chromatographed on a silica gel
column (CH2Cl2 as the eluent); two fractions were collected.
The first fraction contained a mixture of complexes 2 and 3; the
second fraction, complex 4. After recrystallization of the first
fraction from hexane, complex 3 was isolated as paleꢀyellow
crystals (161.6 mg, 18%); complex 2 (53.7 mg, 4%), as darkꢀ
red crystals. Complex 2. Found (%): C, 32.39; H, 1.24.
C
36H16O8Ru6. Calculated (%): C, 32.19; H, 1.19. Complex 3.
Found (%): C, 58.91; H, 4.61. C44H40O8Ru2. Calculated (%):
C, 58.79; H, 4.45. After recrystallization of the second fraction
from a hexane—CH2Cl2 mixture, complex 4 was isolated
(182 mg, 25%) as paleꢀyellow crystals. Complex 4. Found (%):
C, 42.39; H, 3.79; N, 3.65. C26H28N2O10Ru2. Calculated (%):
C, 42.74; H, 3.83; N, 3.83. 1H NMR of ligand 1 (δ): 1.91 (s, 3 H,
Me); 3.26 (t, 4 H, CH2N); 3.51 (t, 4 H, CH2O); 6.68 (s, H,
C=CH); 7.18—7.24 (m, 5 H, Ph).
Xꢀray diffraction study of complexes 2—4. Crystallographic
data and the refinement statistics for compounds 2—4 are given
in Table 4. The structures were solved by direct methods and
refined by the fullꢀmatrix leastꢀsquares method against F 2
Experimental
The 1H NMR spectra were recorded on a Bruker AMXꢀ400
spectrometer (400.13 MHz) in CDCl3 with the use of residual
signals of chloroform (δ 7.25) as the internal standard. The
IR spectra were measured on a Specord IRꢀ75 spectrophotomꢀ
eter. The reactions were carried out under argon. The chroꢀ
matographic separation was performed in air. The preparaꢀ
tive separation was performed with the use of silica gel L
(100—160 µm) (Chemapol). The organic solvents were distilled
under argon over the corresponding drying agents.
hkl
with anisotropic displacement parameters for all nonhydrogen
atoms, except for the atoms of the disordered morpholine fragꢀ
ment in the structure of 4. For compounds 2 and 4, multiscan
Reaction of Ru3(CO)12 with compound 1. Synthesis of bis(µ ꢀ
η ꢀ2ꢀbenzoylꢀ2ꢀmethylethynylidene)hexadecacarbonylhexaꢀ
4
2
Table 4. Crystallographic data and the refinement statistics for compounds 2—4
Parameter
2
3
4
Molecular formula
Molecular weight
Space group
C36H16O18Ru6
1342.91
C2/c
C44H40O8Ru2
898.90
P–1
C26H28N2O10Ru2•CH2Cl2
815.57
Pbcm
Temperature/K
120
293
120
a/Å
b/Å
c/Å
α/deg
15.897(3)
9.778(2)
24.653(4)
—
92.819(4)
—
3828(1)
4
2.330
8.760(2)
10.672(2)
11.684(2)
99.29(2)
110.36(2)
102.02(2)
968.5(4)
1
8.582(1)
19.406(3)
18.544(3)
—
β/deg
—
—
γ/deg
V/Å3
3088.4(8)
4
1.754
Z
dcalc/g cm–3
1.541
8.33
µ/cm–1
23.88
12.08
Diffractometer (λ(MoꢀKα) = 0.71073 Å)
Scanning mode
«SMART 1000»
«Siemens P3/PC»
«SMART 1000»
ω
θ/2θ
ω
Absorption correction, Tmin/Tmax
2θmax/deg
0.796/0.954
56
—
58
0.698/0.927
46
Number of independent reflections (Rint
)
4632 (0.0816)
2737
5099 (0.0213)
4104
2173 (0.1187)
1512
Number of observed reflections with I > σ(I )
R1 (based on F for reflections with I > 2σ(I ))
wR2 (based on F 2 for all reflections)
Number of parameters in refinement
GOOF
0.0445
0.0897
272
0.0280
0.0580
247
0.0846
0.1912
207
0.870
0.902
1.101

2148
Russ.Chem.Bull., Int.Ed., Vol. 55, No. 12, December, 2006
Shtel´tser et al.
absorption corrections were applied based on equivalent reflecꢀ
tions with the use of the SADABS program.16 For complex 3,
absorption was ignored. The structure of 4 contains a dichloroꢀ
methane solvate molecule. The H atoms were placed in geoꢀ
metrically calculated positions and refined using a riding
model. All calculations were carried out on a PC with the use of
the program packages.17,18
Rybinskaya, Izv. Akad. Nauk, Ser. Khim., 2002, 1610 [Russ.
Chem. Bull., Int. Ed., 2002, 51, 1754].
7. C. S. W. Lau and W. T. Wong, J. Chem. Soc., Dalton Trans.,
1998, 3391.
8. G. Jia, D. W. Meek, and J. C. Gallucci, Organometallics,
1990, 9, 2549.
9. S. Komiya, A. Yamamoto, and S. Ikeda, Bull. Chem. Soс.
Jpn, 1975, 48, 101.
10. L. Xu and Y. Sasaki, J. Organomet. Chem., 1999, 585, 246.
11. G. R. Grooks, B. F. G. Johnson, J. Lewis, I. G. Williams,
and G. Gamlen, J. Chem. Soc., A, 1969, 2761.
12. C. M. Kepert, G. B. Deacon, L. Spiccia, G. D. Fallon,
B. W. Skelton, and A. H. White, J. Chem. Soc., Dalton Trans.,
2000, 2867.
This study was financially supported by the Russian
Foundation for Basic Research (Project No. 04ꢀ03ꢀ
32371).
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Received April 24, 2006;
in revised form September 19, 2006