Triruthenium complexes obtained in the thermal reaction of Ru 3(CO)12 with dibenzylideneacetone

Article abstract of DOI:10.1007/s11172-011-0016-z

The complexes Ru₂(CO)₆(μ-H)(O=C(CH=CHPh)C(H)=CPh) (5), Ru₃(CO)₈-(O=C(CH=CHPh)C(H)=CPh)₂ (6), and Ru₃(CO)₇(O=C(CH=CPh)C(H)=CPh)-(O=C(CH₂-CH ₂Ph)C(H)=CPh) (7) were obtained in the reaction of Ru ₃(CO)₁₂ with dibenzylideneacetone PhCH=CHCOCH=CHPh. The structures of complexes 5 and 6 were established by NMR and IR spectroscopy and elemental analysis. The structure of complex 7 was established by X-ray diffraction. The structural and spectroscopic features of the complexes, as well as their possible formation and interconversion pathways are discussed.

Full text of DOI:10.1007/s11172-011-0016-z

Russian Chemical Bulletin, International Edition, Vol. 60, No. 1, pp. 118—123, January, 2011
118
Triruthenium complexes obtained in the thermal reaction
of Ru3(CO)12 with dibenzylideneacetone
S. V. Osintseva, N. A. Shtel´tser, 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 (499) 135 5085. Eꢀmail: cbeta@ineos.ac.ru
The complexes Ru2(CO)6(μꢀH)(O=C(CH=CHPh)C(H)=CPh) (5), Ru3(CO)8ꢀ
(O=C(CH=CHPh)C(H)=CPh)2 (6), and Ru3(CO)7(O=C(CH=CPh)C(H)=CPh)ꢀ
(O=C(CH2—CH2Ph)C(H)=CPh) (7) were obtained in the reaction of Ru3(CO)12 with
dibenzylideneacetone PhCH=CHCOCH=CHPh. The structures of complexes 5 and 6 were
established by NMR and IR spectroscopy and elemental analysis. The structure of complex 7
was established by Xꢀray diffraction. The structural and spectroscopic features of the complexꢀ
es, as well as their possible formation and interconversion pathways are discussed.
Key words: dodecacarbonyltriruthenium, dibenzylideneacetone, fiveꢀmembered oxaꢀ
ruthenacycles, polynuclear complexes, Xꢀray diffraction study, IR spectroscopy, NMR specꢀ
troscopy.
Understanding of the processes occurring upon reacꢀ
tored by following the changes in the IR spectra of the reacꢀ
tions of chemical compounds is one of the main tasks of
chemistry, which could be solved by isolation of the maxꢀ
imum number of reaction products and establishment of
their possible interconversion pathways in the course of
the reaction. We are studying the reactions of oxadienes
with Ru3(CO)12. Variation of the substituents showed that
the major products contain fiveꢀmembered oxaruthenaꢀ
cycles and dihydropyran rings.1 The features of the subꢀ
stituents´ nature have an impact on the structures of miꢀ
nor products. Introduction of new functional groups proꢀ
vides additional possibilities for the coordination to metal
atoms and allows one to expect the formation of complexes
with unusual coordination modes of an organic ligand.2—4
Earlier,4 we have studied the reaction of Ru3(CO)12
with dibenzylideneacetone PhCH=CHCOCH=CHPh
(DBA) (1), which, in contrast to oxadienes, contains two
olefin groups. After longꢀterm heating of the reaction mixꢀ
ture (until Ru3(CO)12 disappeared and the constant IR
spectrum was obtained), complexes 2—4 were isolated
from the reaction mixture (Scheme 1),4 whose structures
were characterized by Xꢀray diffraction.
tion mixture in the region of the metalꢀcarbonyl stretching
vibrations. The production of new complexes was controlled
by the appearance of the IR absorption bands typical of
each complex. Novel complexes 5—7 (Scheme 2) and
small amounts of complexes 2 and 3 were isolated by chroꢀ
matography. The structures of complexes 5 and 6 were
established based on the similarity of the IR spectral charꢀ
acteristics with those of the complexes that have been
synthesized and characterized by us earlier by Xꢀray difꢀ
fraction (Table 1). The IR spectra of both complexes conꢀ
tain the bands of the metalꢀcarbonyl stretching vibrations,
which virtually coincide with their analogs (in the numꢀ
ber, position, and relative intensity).
The 1H NMR spectrum of complex 5 contains
two characteristic signals for the olefinic and hydride
protons appearing as doublets at δ 3.27 and –12.20
(J = 0.9 Hz). The signals are close to those of the complex
Ru2(CO)6(μꢀH)[O=C(CH3)C(H)=CPh] (see Table 1),
whose structure was established by Xꢀray diffraction. Thus,
complex 5 is a binuclear complex where the ruthenium
atoms are linked through the М—М bond, μꢀhydride
bridge, and the oxadiene fragment of the ligand, which
forms with one ruthenium atom the chelate fiveꢀmemꢀ
bered oxaruthenacycle η3ꢀcoordinated to the second ruꢀ
thenium atom. The second olefin group is free of coordiꢀ
nation.
The complexes contain not only the fiveꢀmembered
oxaruthenacycles and dihydropyran rings, but also novel
unusual fragments, viz., η4ꢀdiene and η4ꢀoxadiene ones.
Since it is known that, under drastic reaction conditions,
the products formed initially undergo subsequent transꢀ
formations,5 we studied in the present work the processes
occuring in the initial reaction steps.
1
The H NMR spectrum of complex 6 contains one
characteristic signal at δ 4.91 in the region corresponding
to the signals for the protons of oxaruthenacycles involved
in the η3ꢀcoordination to the ruthenium atom. Such
The reaction of Ru3(CO)12 with DBA was performed
in boiling heptane. The course of the process was moniꢀ
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 114—118, January, 2011.
1066ꢀ5285/11/6001ꢀ118 © 2011 Springer Science+Business Media, Inc.

Triruthenium complexes with the oxadiene ligands
Russ.Chem.Bull., Int.Ed., Vol. 60, No. 1, January, 2011
119
Scheme 1
Conditions: refluxing, 4 h.
a characterisitc spectral pattern corresponds to the
dination. To conclude, complexes 5 and 6 formed in the
initial reaction steps are analogous to those obtained in
the reactions with oxadienes; the second olefin group of
DBA has no effect on the behavior of the oxadiene fragꢀ
ment and acts only as a substituent.
Complex 7 was isolated from the reaction mixture toꢀ
gether with complexes 5 and 6 and observed in later reacꢀ
tion steps.4 The structure of complex 7 was established by
the Xꢀray diffraction analysis, which showed that two
ligand molecules are involved in the coordination to three
trinuclear complexes of
a
general formula
Ru3(CO)8[O=C(R´)C(H)=CR″]2 (see Table 1), whose
structures were established by the Xꢀray diffraction analyꢀ
sis. Thus, complex 6 contains the trinuclear metal chain
where two terminal ruthenium atoms are chelated by the
oxadiene fragments of the two ligands to form oxaruthenaꢀ
cycles. Both oxaruthenacycles η3ꢀcoordinate to the cenꢀ
tral ruthenium atom. In contrast to complex 2, one of
each CН=CН groups of both ligands is involved in coorꢀ
Scheme 2
Conditions: refluxing, 2—3 h.

120
Russ.Chem.Bull., Int.Ed., Vol. 60, No. 1, January, 2011
Osintseva et al.
Table 1. IR and NMR spectra of the complexes obtained
Compound
IR
1Н NMR
δ, (C6D6), J/Hz
ν(CО)/cm–1(hexane)
(PhCH=CH)2CO
(PhCH2CH2)2CO
5
1668 m, 1610 s
7.08 (d, 1 H, CH=CH, J = 16.0); 7.35—7.62
(m, 5 H, Ph); 7.74 (d, 1 H, CH=CH, J = 16.0)
1684 m, 1612 s
2.76 (t, 2 Н, СН2, J = 7.8); 2.94 (t, 2 Н, СН2,
J = 7.8); 7.35—7.62 (m, 5 H, Ph)
2098 s, 2064 v.s, 2038 s,
2016 v.s, 2008 s, 1980 m
–12.20 (d, 1 H, Ru—H, J = 0.9); 3.27 (d, 1 H,
CH=C, J = 0.9); 6.86 (d, 1 H, CH=CН,
J = 16.0); 6.98—7.65 (m, 11 H, Ph, CH=CH)
Ru2(CO)6(μꢀH)[O=C(CH3)С(H)=CPh]a,b
6
2098 s, 2062 v.s, 2038 s,
2014 v.s, 2004 s, 1982 m
–12.50 (d, 1 H, Ru—H, J =1); 2.12 (s, 3 Н);
3.55 (d, 1 H, CH=C, J =1); 7.0—7.6 (m, 5 H, Ph)
2086 s, 2074 v.s, 2024 v.s,
1998 s, 1938 w
4.91 (s, 1 H, CH=C); 6.72 (d, 1 H, CH=CН,
J = 16.0); 6.62—8.10 (m, 12 H, Ph, CH=CH)
Ru3(CO)8(O=C(Tol)С(H)=CPh)2* (6´)a,b
Ru3(CO)8(O=C(Fc)С(H)=CFc)2* (6″)a,c
2088 s, 2074 v.s, 2020 v.s,
1996 s, 1934 w
2.36 (s, 3 Н); 3.45 (s, 1 H); 6.8—7.1 (m, 9 H, Ph)
2078 s, 2064 v.s, 2008 v.s,
1980 s, 1946 w
3.64 (s, 1 H); 3.93 (m, 1 H); 4.13 (s, 5 H); 4.19
(s, 5 H); 4.29 (m, 1 H); 4.40 (m, 1 H); 4.46 (m, 1 H);
4.56 (m, 2 H); 4.63 (m, 1 H); 4.67 (m, 1 H)
7
2092 s, 2042 v.s, 2032 s,
2008 s, 1990 m, 1980 m
2.01 (s, 1 H, CH=C); 2.23 (t, 2 Н, CН2, J = 7.6);
2.83 (t, 2 Н, CН2, J = 7.6); 4.48 (s, 1 H, CH=C);
4.59 (d, 1 H, CH=C, J = 13.8); 5.66 (d, 1 H,
CH=C, J = 13.8); 6.61—8.11 (m, 20 H, Ph)
a 1H NMR spectra were recorded in CDCl3. The data from Ref. 6. b The data from Ref. 1. c The data from Ref. 7.
metal atoms (Fig. 1, Table 2 and 3). The open metal chain
contains two Ru—Ru bonds. Each ligand chelates one of
the terminal ruthenium atoms to form the fiveꢀmembered
ruthenacycle. The oxaruthenacycles η3ꢀcoordinate to the
central ruthenium atom. This structural fragment is comꢀ
mon for complexes 2, 6, and 7. The complexes differ in
the states of the olefin groups that are not involed in chelaꢀ
tion. In complex 6, both the olefin groups are free of coorꢀ
dination. In complex 2, both the olefin groups πꢀcoordiꢀ
nate to the ruthenium atom. In complex 7, one of the
olefin groups πꢀcoordinate to the ruthenium atom (as in
complex 2) and the second olefin group is reduced to
CН2—CН2. It should be noted that, upon the formation
of oxaruthenacycle in the reactions of Ru3(CO)12 with
both oxadienes and DBA, the ligand molecule loses the
hydrogen atom, whereas the ligand in excess amounts act
as the hydrogen acceptor and is reduced to the saturated
ketones.4 However, we have been unsuccessful earlier in
isolating products from the reactions with oxadienes,
which would contain the completely or partially reduced
ligand as is observed in complex 7.
transforms upon heating into a mixture of other unidentiꢀ
fied products (see Experimental). In order to understand
the reason, we considered the spatial arrangement of the
ligands around the central ruthenium atoms in complexes
2, 6, and 7 (see Ref. 8). The structure of complex 6 was not
established by Xꢀray diffraction, but the structures of analꢀ
ogous complexes isolated in the reactions of Ru3(CO)12
with 1ꢀpꢀtolylꢀ3ꢀphenylpropꢀ2ꢀenꢀ1ꢀone (6´)1 and 1,3ꢀdiꢀ
ferrocenylpropꢀ2ꢀenꢀ1ꢀone (6″)7 have been determined
Thus, the chain trinuclear clusters 2, 6, and 7 having
similar structures were isolated in different steps of the
reaction of Ru3(CO)12 with DBA. We assumed that the
nonꢀcoordinated olefin groups of complex 6 can undergo
πꢀcoordination upon heating under the reaction condiꢀ
tions to form complex 2 or reduction to form complex 7.
However, the control experiments showed that complex 6

Triruthenium complexes with the oxadiene ligands
Russ.Chem.Bull., Int.Ed., Vol. 60, No. 1, January, 2011
121
C(39)
C(38)
C(40)
C(21)
C(13)
C(20)
C(41)
C(37)
C(14)
C(15)
C(12)
C(36)
C(25)
C(22)
C(34)
O(9)
C(19)
C(18)
C(35)
C(11)
C(10)
C(23)
O(3)
C(9)
C(17)
C(16)
C(24)
C(26)
C(8)
O(6)
C(3)
C(6)
O(8)
Ru(2)
Ru(3)
C(4)
Ru(1)
C(27)
C(28)
O(4)
C(7)
C(2)
O(2)
C(1)
C(33)
C(5)
C(29)
O(7)
C(32)
O(5)
C(30)
O(1)
C(31)
Fig. 1. Molecular structure of complex 7 (the minor part of the disordered CH2CH2Ph fragment and all hydrogen atoms are
not shown).
earlier. Based on the analysis of the structures of two latter
complexes, it was concluded that, when passing from the
aryl substituent to the ferrocenyl one, the relative disposiꢀ
tion of ligands in the coordination sphere of the central
ruthenium atom remains unchanged. This allows us to
assume that the passage to the styryl substituent in comꢀ
plex 6 will not change the spatial arrangement of ligands.
The central ruthenium atoms in complexes 2, 6, and 7
have a pseudoꢀoctahedral ligand environment. The termiꢀ
nal ruthenium atoms are in the transꢀposition to each other
in complex 6 and in the cisꢀposition in complexes 2 and 7.
The πꢀcoordinated C=C bonds in the oxaruthenacycle are
in the transꢀposition to each other in complex 2 and in the
cisꢀposition in complexes 6 and 7. The mutual disposition
of two oxaruthenacycles relative to the central ruthenium
atom is different in all complexes. Therefore, transformaꢀ
tions of complexes cannot occur without cleavage of sevꢀ
eral bonds, which allows one to conclude that the formaꢀ
Table 3. Bond angles (ω) for complex 7
Angle
ω/deg
Ru(2)—Ru(1)—Ru(3)
C(10)—Ru(2)—O(8)
C(8)—O(8)—Ru(2)
O(8)—C(8)—C(9)
115.81(2)
81.7(2)
Table 2. Principal bond lengths (d) for complex 7
111.4(3)
118.2(4)
116.7(4)
108.5(3)
131.0(5)
121.4(4)
81.6(2)
109.8(3)
121.5(4)
115.7(5)
109.1(4)
114.3(6)
113.6(6)
Bond
d/Å
Bond
d/Å
C(10)—C(9)—C(8)
C(9)—C(10)—Ru(2)
C(18)—C(17)—C(8)
C(17)—C(18)—C(19)
C(27)—Ru(3)—O(9)
C(25)—O(9)—Ru(3)
O(9)—C(25)—C(26)
C(25)—C(26)—C(27)
C(26)—C(27)—Ru(3)
C(35)—C(34)—C(25)
C(34)—C(35)—C(36)
Ru(1)—Ru(2)
Ru(1)—Ru(3)
Ru(1)—C(9)
Ru(1)—C(10)
Ru(1)—C(26)
Ru(1)—C(27)
Ru(2)—C(10)
Ru(2)—O(8)
Ru(3)—C(27)
Ru(3)—O(9)
2.7966(8)
2.8741(9)
2.345(5)
2.248(5)
2.239(5)
2.189(5)
2.076(5)
2.088(3)
2.046(5)
2.122(3)
Ru(3)—C(17)
Ru(3)—C(18)
O(8)—C(8)
2.264(5)
2.336(5)
1.249(5)
1.488(7)
1.394(6)
1.385(6)
1.285(6)
1.418(7)
1.445(6)
1.487(9)
C(8)—C(9)
C(9)—C(10)
C(17)—C(18)
O(9)—C(25)
C(25)—C(26)
C(26)—C(27)
C(34)—C(35)

122
Russ.Chem.Bull., Int.Ed., Vol. 60, No. 1, January, 2011
Osintseva et al.
plex X (hexane), ν(CО)/cm–1: 2068 m, 2048 v.s, 2032 s, 2018 m,
2008 m, 1988 s, 1962 w. By elution with a petroleum ether—
benzene (1 : 1) mixture, complex 7 (15 mg, 4.9%) and complexꢀ
es 2 and 3 (negligible amounts) were isolated.
Complex 5. Found (%): C, 46.02; Н, 2.45. C23Н14O7Ru2.
Calculated (%): C, 45.73; Н, 2.34.
Complex 6. Found (%): C, 51.20; Н, 2.69. C42Н26O10Ru3.
Calculated (%): C, 50.92; Н, 2.65.
2, 6´, 6″, 7
Table 4. Selected bond lengths and angles for complexes 2, 6´,
6´´, and 7
Complex 7. Found (%): C, 51.20; Н, 3.09. C41Н29O9Ru3.
Calculated (%): C, 51.00; Н, 3.03. The fine redꢀorange crystals
of complex 7 were obtained by recrystallization from a benzeneꢀ
hexane mixture.
B. A mixture of Ru3(CO)12 (320 mg, 0.5 mmol) and comꢀ
pound 1 (468.5 mg, 2 mmol) in heptane (150 mL) was refluxed
for 3 h. Same as previous, by elution with petroleum ether,
Ru3(CO)12 (100 mg), complex 5 (5 mg, 2.6%), the oily complex
X (20 mg), which was characterized by the spectra analogous to
those of complex X obtained as described above, and complex 6
(20 mg, 6.4%) were obtained. By elution with a petroleum ehter—
benzene (1 : 1) mixture, complex 7 (20 mg, 6.6%) and complexꢀ
es 2 and 3 (negligible amounts) were isolated.
Reaction of complex 6 with dibenzylideneacetone (1). A mixꢀ
ture of complex 6 (12.5 mg, 0.01 mmol) and compound 1 (10 mg,
0.04 mmol) in heptane (20 mL) was refluxed for 1 h. After heatꢀ
ing for 20 min, the IR spectrum of an unidentified compound
was observed (hexane), ν(CО)/cm–1: 2046 m, 2020 m, 2012 m,
1978 m, 1956 m). No traces of complexes 2 and 7 were detected.
Further heating resulted in no changes in the IR spectrum.
Xꢀray diffraction study. The crystals of 7•C6H6 (C47H34O9Ru3,
M = 1045.95) are triclinic, space group P–1 0303, at 120 K
a = 7.927(2), b = 12.583(3), c = 21.065(5) Å, α = 98.877(5),
β = 94.175(5), γ = 100.273(5)°, V = 2031.7(9) Å3, Z = 2,
dcalc = 1.710 g cm–3, μ(MoꢀKα) = 11.59 cm–1. The intensities of
20665 reflections (9688 independent reflections, Rint = 0.060)
were measured on a Bruker SMART 1000 CCD autodiffractoꢀ
meter (graphite monochromator, λ(MoꢀKα) = 0.71073 Å,
Compꢀ
lex
Bond/Å
Angle/deg
Ru(1)—Ru(2) Ru(2)...Ru(2´)
ω*
ϕ**
2
2.840
2.802
2.777
4.276
5.390
5.445
4.804
97.7
148.3
157.2
115.8
156.3
67.1
91.6
90.3
6´
6″
7
2.797, 2.874
* The bond angle Ru(2)—Ru(1)—Ru(2´).
** Τhe torsion angle X(1)—Ru(2)—Ru(2´)—X(1´) where X(1) is
the center of the C(2)—C(3) bond and X(1´) is the center of the
C(2´)—C(3´) bond.
tion of complexes occurs independently of each other.
The geometric parameters characterizing the spatial diffeꢀ
rences between complexes 2, 6, and 7 are given in Table 4.
Thus, the reaction of Ru3(CO)12 with DBA affords, in
the initial steps, the products that are typical of the reactions
with oxadienes and the presence of the second olefin group
has no impact on the reaction process. Upon a longerꢀ
term reaction, the complexes are produced, wherein addiꢀ
tional coordination modes of the ligand are implemented.
Experimental
ωꢀscanning, 2θ
= 56°, Т = 120 K). The structure was solved
max
1
by the direct method and refined by the fullꢀmatrix least squares
H NMR spectra were recorded on a Bruker AMXꢀ400
method over F 2 with the anisotropic thermal parameters for
hkl
(400.13 MHz) spectrometer in CDCl3 and C6D6 using the residꢀ
all nonꢀhydrogen atoms. There are two solvate molecules of
benzene in the structure, which are in particular positions on the
inversion centers. The CH2CH2Ph group is disordered over two
positions with population of positions 0.75/0.25. The hydrogen
atoms were placed in the geometrically calculated positions and
included in the refinement in the riding model. The final diverꢀ
gence factors are R1 = 0.0459 (refinement over Fhkl for 5401
reflections with I > 2σ(I)), wR2 = 0.0896, and S = 0.960 (refineꢀ
ment over F2hkl for all independent reflections). All calculations
were performed using the SHELXTL software system.9 The full
tables of atomic coordinates, bond angles, and anisotropic therꢀ
mal parameters were deposited in the Cambridge Crystallographꢀ
ic Data Centre.
ual signals for the incomletely deuterated CDCl3 (δН for CНCl3
is 7.25) and C6D6 (δ for C6НD5 is 7.25) as the internal stanꢀ
Н
dards. IR spectra were recorded on a Specordꢀ75 IR spectrphoꢀ
tometer.
3
2,3,4ꢀη ꢀ(5ꢀPhenylꢀ2ꢀstyrylꢀ1ꢀoxaꢀ2ꢀtricarbonylruthenaꢀ
cyclopentaꢀ3,5ꢀdiene)ꢀμꢀhydridotricarbonylruthenium (5), bisꢀ
3
[2,3,4ꢀη ꢀ(5ꢀphenylꢀ2ꢀstyrylꢀ1ꢀoxaꢀ2ꢀtricarbonylruthenacycloꢀ
3
2
pentaꢀ3,5ꢀdiene)]dicarbonylruthenium (6), and 2,3,4ꢀη ꢀ[η ꢀ2ꢀ
styrylꢀ(5ꢀphenylꢀ1ꢀoxaꢀ2ꢀdicarbonylruthenacyclopentaꢀ3,5ꢀdiꢀ
3
ene)]ꢀ2,3,4ꢀη ꢀ(2ꢀphenylethylꢀ5ꢀphenylꢀ1ꢀoxaꢀ2ꢀtricarbonylruꢀ
thenacyclopentaꢀ3,5ꢀdiene)dicarbonylruthenium (7). A. A mixture
of Ru3(CO)12 (320 mg, 0.5 mmol) and compound 1 (468.5 mg,
2 mmol) in heptane (150 mL) was refluxed for 2 h 20 min. After
cooling to room temperature, the reaction mixture was filtered.
A heptane solution was chromatographed on a silica gel column.
By elution with petroleum ether, Ru3(CO)12 (120 mg), complex
5 (25 mg, 13.3%), complex 6 (10 mg, 3.2%), and an unidentified
This work was financially supported by the Russian
Foundation for Basic Research (Project No. 10ꢀ03ꢀ00505).
1
oily complex X (18 mg) were isolated. Н NMR for complex X
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Received June 8, 2010;
in revised form October 20, 2010