Synthesis of Mo(CO)2(η3-PPh2(o-C 6H4)C(=O)H)2 and its reaction with C 60

Article abstract of DOI:10.1016/j.jorganchem.2011.01.023

Reaction of Mo(CO)₃(NCMe)₃ and PPh ₂(o-C₆H₄)C(O)H (abbreviated as PCHO) at room temperature affords Mo(CO)₂(η³-PCHO)₂ (1), while compound 1 and the phosphine-imine complex Mo(CO)₄(η ²-PPh₂(o-C₆H₄)CHNMe) (2) are obtained by using Mo(CO)₃(η³-(MeNCH₂) ₃) as the reactant. Thermal reaction of 1 with C₆₀ products Mo(CO)₂(η⁴-(PPh₂(o-C ₆H₄)CH)₂)(η²-C₆₀) (3) in low yield, apparently through coupling of the formyl moieties. The structures of 1 and 3 have been determined by an X-ray diffraction study. The two aldehyde groups of 1 and C₆₀ ligand of 3 are coordinated to the molybdenum atom in a π-fashion.

Full text of DOI:10.1016/j.jorganchem.2011.01.023

Journal of Organometallic Chemistry 696 (2011) 1474e1478
Contents lists available at ScienceDirect
Journal of Organometallic Chemistry
journal homepage: www.elsevier.com/locate/jorganchem
3
Synthesis of Mo(CO)2(
h
-PPh (o-C H )C(]O)H) and its reaction with C
60
2
6
4
2
Chi-Shian Chen, Cha-Shie Lin, Wen-Yann Yeh*
Center for Nanoscience and Nanotechnology, National Sun Yat-Sen University, 70 Lien-Hai Road, Kaohsiung 804, Taiwan
a r t i c l e i n f o
a b s t r a c t
Article history:
Received 6 December 2010
Received in revised form
Reaction of Mo(CO) (NCMe) and PPh (o-C H )C(]O)H (abbreviated as PCHO) at room temperature
3
3
2
6 4
3
2
affords Mo(CO)
PPh (o-C ) as the reactant. Thermal
2 2 6 4 2
reaction of 1 with C60 products Mo(CO) (h -(PPh (o-C H )CH) )(h -C60) (3) in low yield, apparently
2
(
h
2 4
-PCHO) (1), while compound 1 and the phosphine-imine complex Mo(CO) (h -
3
2
6
H
4
)CH]NMe) (2) are obtained by using Mo(CO)
3
(
h
-(MeNCH
2
)
3
15 January 2011
4
2
Accepted 18 January 2011
through coupling of the formyl moieties. The structures of 1 and 3 have been determined by an X-ray
diffraction study. The two aldehyde groups of 1 and C60 ligand of 3 are coordinated to the molybdenum
atom in a p-fashion.
Keywords:
Molybdenum complex
Fullerene complex
Aldehyde complex
Aldehyde coupling
Ó 2011 Elsevier B.V. All rights reserved.
1
. Introduction
PCHO)(
h
1-PCHO) and W(CO)
2
(
h
3-PCHO)
-fashion. The analogous reaction
3 2 3
(h -(MeNCH ) ) with two equivalents of PCHO at
2
[12], with the aldehyde
groups coordinating in a unique
p
3
Chelating ligands containing “soft” phosphorus and “hard”
of Mo(CO)
ambient temperature afforded Mo(CO)
Interestingly, an orange side-product was also isolated, character-
ized as Mo(CO)
treating the acetonitrile complex Mo(CO)
3
nitrogen or oxygen donor atoms can alter the reactivity or metal
centers and may be of interest in design and development of new
homogeneous catalytic systems [1e5]. The o-(diphenylphosphino)
2 2
(h -PCHO) (1) in 30% yield.
2
4
(
h
-PPh
2
(o-C
6
H
4
)CH]NMe) (2; 35%). In contrast,
(NCMe) with PCHO
benzaldehyde molecule (PPh
2
(o-C
6
H
4
)C(]O)H; abbreviated as
3
3
PCHO) is one of the simplest bidentate P,O-chelating agents [6].
Usually, the phosphine center is coordinated to the metal in
produced 1 in 35% yield without the formation of 2. The results are
summarized in Scheme 1.
advance of the aldehyde group and can serve as a monodentate
Compound 1 forms air-stable, bright yellow crystals. The FAB
mass spectrum gives the molecular ion at m/z 734 ( Mo), corre-
1
98
h
-P donor [7,8]. On the other hand, the PCHO ligand can act as
a
chelating phosphineealdehyde, with the aldehyde moiety
sponding to a Mo(CO)
spectrum displays two CO absorptions at 1976 and 1918 cm
suggesting a cis-arrangement for the two carbonyl ligands. The free
2
segment plus two PCHO molecules. The IR
ꢀ
1
bonded to the metal in a
or in a -fashion through the C]O double bond [11,12]. Recently,
synthesis of fullerene-bound organometallic complexes has been
afocalpointofmanyresearchtopics,duetotheirpotentialapplication
in biological, magnetic, electronic, catalytic and optical devices
s-fashion through the oxygen atom [9,10],
,
p
31
PCHO ligand presents a P resonance at ꢀ11.37 ppm for the
1
phosphorus atom and an H resonance at 10.50 ppm for the formyl
31
proton, while compound 1 displays one P resonance at 18.04 ppm
and the formyl proton resonance is shift upfield to 5.38 ppm. These
spectral data suggest a same coordination mode for the two PCHO
ligands.
[13e16]. In this paper, we present a new molybdenum complex
bearing -bonded formyl groups and show its reaction with C60
p
.
The molecular structure of 1 is depicted in Fig. 1. The Mo center is
coordinated by two terminal carbonyl ligands and two PCHO ligands.
Taking the centers of the aldehyde C]O bond, the phosphorus
atoms and the carbonyl groups, the coordination about the Mo atom
can be described as a distorted octahedron. The two carbonyl ligands
2
. Results and discussion
Previously, reactions of the triazacyclohexane complex W
3
3
(
3 2 3 3
CO) (h -(MeNCH ) ) with PCHO were shown to give W(CO) (h -
ꢁ
are in cis positions, with the C1eMoeC2 angle of 86.3(2) . The
ꢀ
average MoeCO length is 1.99 A, and the average MoeCeO angle is
ꢁ
1
h
75.5 . The two PCHO ligands are coordinated to the Mo atom in an
3
-fashion. The two P atoms are cis to each other, with MoeP1 and
MoeP2 distances of 2.5652(9) and 2.593(1) A, respectively, and the
*
Corresponding author. Fax: þ886 7 5253908.
ꢀ
E-mail address: wenyann@mail.nsysu.edu.tw (W.-Y. Yeh).
0
022-328X/$ e see front matter Ó 2011 Elsevier B.V. All rights reserved.
doi:10.1016/j.jorganchem.2011.01.023

C.-S. Chen et al. / Journal of Organometallic Chemistry 696 (2011) 1474e1478
1475
Me
O
C
H
O
C
Me
H
N
O
O
Me
O
C
O
Me
N
N
N
Mo
OC
H
Mo
Mo
+ 2
+
P
P
H
Ph
C
O
C
C
2
Ph P
O
P
O
Ph
C
O
C
Ph
Ph
Ph Ph
O
1
2
Me
C
N
Me
Me
C
O
C
N
N
H
+
2
Mo
1
C
C
O
Ph
2
P
O
C
O
Scheme 1. Preparation of 1 and 2.
ꢁ
P1eMoeP2 angle is 100.12(3) . The trans angles P1eMoeC2 167.2
Mo to the p* orbital of the C]O double bond. The C3eO3 and
ꢁ
ꢁ
(
1) and P2eMoeC1 165.3(1) are deviated significantly from line-
arity (180 ) and could be attributed to steric congestion surrounding
the Mo atom. The two aldehyde groups are in trans positions and are
C22eO4 vectors, which are bent away from the adjacent arene
ꢁ
ꢁ
planes by an average of 54 , are approximately perpendicular to each
ꢁ
other (88 ), presumably to obtain better
p
back-donation from
p
-bonded to the Mo atom, with the distances C3eMo 2.215(4),
separate filled d orbitals of the Mo metals.
ꢀ
O3eMo 2.088(2), C22eMo 2.232(4), and O4eMo 2.086(2) A. The
angles C4eC3eO3 118.4(3) and C23eC22eO4 120.5(3) are close to
the ideal value of 120 for an sp hybrid C atom. However, the
distances C3eO3 1.335(4) A and C22eO4 1.323(4) A are ca. 0.1 A
longer than the pendant formyl distance founded in W(CO)
PCHO)(
The IR spectrum of 2 in the carbonyl region shows three
ꢁ
ꢁ
ꢀ1
stretching absorptions at 2016, 1903, and 1855 cm , with the
ꢁ
2
0
31
pattern resemble to a cis-M(CO)
4
LL composition [17,18]. The
P
ꢀ
ꢀ
ꢀ
1
{ H} NMR spectrum shows a downfield signal at 36.3 ppm, while
the H NMR spectrum presents a 1H singlet at 8.21 ppm, a multiplet
3
1
3
(h
-
1
h
-PCHO) [12], suggesting a significant
p
back-donation from
(14H) in the range 7.54e6.85 ppm, and a 3H singlet at 3.74 ppm.
Because of the absence of diagnostic spectral features to reveal its
structure, a single-crystal X-ray diffraction study was performed.
An ORTEP drawing of 2, shown in Fig. 2, consists of a Mo(CO)
4
fragment bonded with an iminophosphine group. It turns out that
compound 2 (and its crystal structure) is known [19], previously
prepared from Mo(CO)
NMe ligand directly. Yet the origin of MeN fragment in 2 remains
interesting. Since PCHO does not react with free (MeNCH
4 2 2 6 4
(piperidine) and the PPh (o-C H )CH]
2 3
)
ꢀ
ꢁ
Fig. 1. Molecular structure of 1. Selected bond distances (A) and bond angles ( ):
MoeP1 2.5652(9), MoeP2 2.593(1), MoeC1 1.995(5), MoeC2 1.988(4), MoeC3 2.215
(
1
4), MoeO3 2.088(2), MoeC22 2.232(4), MoeO4 2.086(2), C3eO3 1.335(4), C22eO4
.323(4) and P1eMoeC2 167.2(1), P2eMoeC1 165.3(1), C3eMoeC22 153.3(1),
C3eMoeO3 36.0(1), O3eMoeO4 155.7(1), O4eMoeC22 35.5(1), C9eP1eMo 101.5(1),
C28eP2eMo 99.7(1), C23eC22eO4 120.5(3), C4eC3eO3 118.4(3), O1eC1eMo 175.2
Fig. 2. ORTEP diagram of 2. This structure is identical to that previously determined [19].
(
4), O2eC2eMo 175.8(4).

1476
C.-S. Chen et al. / Journal of Organometallic Chemistry 696 (2011) 1474e1478
molecule at room temperature and the reaction of Mo(CO)
3
(N-
CMe) with PCHO does not produce 2, the iminophosphine ligand
3
of 2 is apparently generated by a Mo-mediated Schiff-base con-
densation [20e22] and rearrangement reactions of PCHO and
(
MeNCH
mentation of (MeNCH
NMe) ] ligand has been observed in the triosmium system [23,24].
The attachment of C60 to organometallic complexes is an
2
)
3
species, though the mechanism is still unclear. Frag-
2 3
)
molecule to generate an amidino [CH
(
2
important area within fullerene chemistry. Compound 1 was
therefore reacted with C60 in refluxing chlorobenzene to generate
4
2
a new fullerene complex Mo(CO)
2 2 6 4 2
(h -(PPh (o-C H )CH) )(h -C60)
(3) (Scheme 2), but in low yield. Most of 1 decomposes under such
harsh conditions, and there are no reactions with the temperatures
ꢁ
below 100 C. The MALDI mass spectrum of 3 displays the highest
ion peak at m/z 1390 (98Mo), corresponding to the [M eCO] frag-
þ
ment, and the isotope distribution matches the calculated pattern.
1
The H NMR spectrum shows a multiplet (24H) in the range
7
.83e6.99 ppm and a triplet signal (2H, JPeH ¼ 6 Hz) at 4.30 ppm,
31 1
and the P{ H} NMR spectrum presents one signal at 52.59 ppm.
The molecular structure of 3 is illustrated in Fig. 3, in which the
molybdenum atom is bonded to two terminal CO, a C60, and
2 6 4 2
a (PPh (o-C H )CH) ligand in a distorted octahedral fashion. The
ꢀ
ꢁ
two phosphine and the two carbonyl groups are trans to each other,
Fig. 3. Molecular structure of 3. Selected bond distances (A) and bond angles ( ):
MoeP1 2.516(2), MoeP2 2.512(1), MoeC1 2.038(6), MoeC2 2.023(7), MoeC21 2.317
(
1
1
ꢁ
with the angle C1eMoeC2 177.6(3) being close to linearity, while
6), MoeC22 2.335(5), MoeC41 2.283(6), MoeC42 2.288(5), C1eO1 1.153(6), C2eO2
.141(6), C21eC22 1.418(7), C41eC42 1.497(8) and MoeC1eO1 176.0(5), MoeC1eO2
77.5(6), MoeP1eC15 103.8(2), MoeP2eC28 104.0(2), P1eMoeP2 154.05(6),
P1eMoeC1 90.4(2), P1eMoeC2 89.3(2), C1eMoeC2 177.6(3), P2eMoeC1 93.5(2),
P2eMoeC2 87.8(2), C21eC22eC23 120.0(6), C22eC21eC20 118.5(5).
ꢁ
the P1eMoeP2 angle (154.05(6) ) shows a substantial distortion
(
C
Fig. 4) and may be attributed to steric interactions with the bulky
ꢀ
60 group. The bond lengths MoeP1 2.516(2) and MoeP2 2.512(1) A
ꢀ
are 0.06 A shorter than those observed for 1, while the MeCO
ꢀ
ꢀ
distances (2.038(6) and 2.023(7) A) are 0.04 A longer, consistent
with the stronger net -accepting capacity of the CO ligand
compared with P(aryl)
denum atom in an
MoeC41 2.283(6) A and MoeC42 2.288(5) A. The distance C41eC42
p
3 2 3
On the other hand, Mo(CO) (h ) ) and 1 show higher
3-(MeNCH
3
. The C60 moiety is bound to the molyb-
2
chemical reactivity than their tungsten analogues, consistent with
the characteristic that the second-row transition metal complexes
are usually more reactive than either of those containing first- or
third-row elements [26]. Finally, despite the low yield of 3, the
reaction of 1 and C60 leads to coupling of PCHO ligands is unique
within metal-fullerene chemistry.
h
-fashion through a 6:6-ring junction with
ꢀ
ꢀ
ꢀ
ꢀ
1
.497(8) A is elongated (ca. 0.12 A) in comparison with other
unperturbed 6:6-double bonds and is attributed to back-donation
from the molybdenum atom. The most striking feature is the
formation of trans-PPh (o-C )CH]CH(o-C )PPh species
p
2
6
H
4
6
H
4
2
which is likely from coupling of two PCHO ligands concomitant
with loss of two oxygen atoms; the results are analogous to the
3. Experimental
organic McMurry reaction [25]. The C21]C22 unit is
p
-bonded to
ꢀ
the molybdenum atom with MoeC21 2.317(6) A and MoeC22 2.335
3.1. General methods
ꢀ
ꢀ
(
5) A, which are ca. 0.04 A longer than the opposite MoeC60 bonds.
The C20eC21eC22eC23 atoms are not coplanar to have the
All manipulations were carried out under an atmosphere of
ꢁ
torsional angle 139.1 . The (Mo, C21, C22) and (Mo, C41, C42) planes
purified dinitrogen with standard Schlenk techniques. Mo(CO)
3
ꢁ
3
are about orthogonal, giving a dihedral angle of 85.2(5) .
3 3 2 3
(NCMe) [27], Mo(CO) (h -(MeNCH ) ) [28], and PCHO [6] were
In conclusion, we have prepared compound 1 and presented its
prepared as described in the literature. C60 (99%) was purchased
from Bulky USA. Solvents were dried over appropriate reagents
under dinitrogen and distilled immediately before use. Preparative
thin-layer chromatographic (TLC) plates were prepared from silica
gel (Merck). Infrared spectra were recorded on a Jasco FT/IR-4100 IR
reactivity toward C60. The structure of 1 closely resembles the
3
tungsten analogue W(CO)
2
(h
-PCHO)
2
with the bond lengths and
ꢀ
ꢁ
angles differing to within 0.04 A and 2 , respectively. This is due to
the lanthanide contraction, leading to comparable Mo and W radii.
O
C
H
O
O
Ph
O
C
C
O
Ph
Mo
P
+
C60
P
H
H
Ph
Mo
P
Ph
Ph
Ph
Ph
Ph
C
O
P
3
1
H
Scheme 2. Reaction of 1 and C60
.

C.-S. Chen et al. / Journal of Organometallic Chemistry 696 (2011) 1474e1478
1477
Table 1
Crystal data for 1 and 3.
1
3
Formula
C
40
H30MoO
4
P
2
C
100 2 2 2
H30MoO P $2CS
Crystal system
Formula weight
T (K)
Monoclinic
732.52
295(2)
Monoclinic
1573.38
200(2)
Space group
P2
1
/n
1
P2 /n
ꢀ
a (A)
9.4464(1)
16.9229(2)
21.3523(3)
90
101.5918(8)
90
3343.77(7)
4
1.455
15.175(2)
18.471(3)
23.684(3)
90
99.169(3)
90
6554.0(16)
4
1.595
ꢀ
b (A)
ꢀ
c (A)
ꢁ
a
b
g
( )
ꢁ
( )
ꢁ
( )
ꢀ
3
V (A )
Fig. 4. The coordination environment of molybdenum atom in 1 and 3.
Z
D
m
3
calc (Mg/m )
ꢀ
1
(mm
)
0.53
0.440
spectrometer. 1H and 31P NMR spectra were obtained on a Varian
R
1
/
w
R
2
0.050/0.136
1.006
0.0666/0.1096
0.961
2
GOF on F
Unity INOVA-500 spectrometer at 500 and 202.5 MHz, respectively.
Fast-atom-bombardment (FAB) mass spectra and Matrix-assisted
laser desorption ionization (MALDI) mass spectra were recorded on
a JEOL JMS-SX102A and Bruker Microflex-LT mass spectrometer,
respectively. Elemental analyses were performed at the National
Science Council Regional Instrumentation Center at National Chen-
Kung University, Tainan, Taiwan.
introduced into the flask via a syringe and the solution was stirred
at room temperature for 24 h. The solvent was removed on
a rotary evaporator and the residue was subjected TLC, with
dichloromethane/n-hexane (1:1, v/v) as eluant. Compound 1 was
isolated from the major pale yellow band (100 mg, 35%).
3
.2. Reaction of Mo(CO)
3
(h
3-(MeNCH
3-(MeNCH
2 3
) ) (120 mg, 0.388 mmol) and PCHO
2 3
) ) and PCHO
3.4. Thermal reaction of 1 and C
60
3
Mo(CO) (h
(
280 mg, 0.965 mmol) were placed in an oven-dried 100 ml Schlenk
Compound 1 (30 mg, 0.041 mmol) and C60 (29 mg, 0.044 mmol)
were placed in an oven-dried 100 ml Schlenk flask, equipped with
a reflux condenser, and chlorobenzene (10 ml) was introduced into
the flask via a syringe. The mixture was refluxed under dinitrogen
for 30 min, resulting a brownish green solution. The solvent was
removed under vacuum, and the residue was subjected to TLC, with
flask under a dinitrogen atmosphere. Dichloromethane (40 ml) was
introduced into the flask via a syringe and the mixture was stirred at
room temperature for 24 h, resulting in an orange-red solution. The
solvent was removed on a rotary evaporator and the residue was
subjected TLC, with dichloromethane/n-hexane (1:1, v/v) as eluant.
Isolation of the material forming the second orange band afforded
Mo(CO)
the material forming the fourth pale yellow band afforded air-stable,
yellow crystals of Mo(CO) (h -PCHO) (1; 85 mg, 30%).
2 2
2
2
CS as eluant. The first purple band recovered C60 (19 mg) in 66%.
4
(h
2 6 4
-PPh (o-C H )CH]NMe) (2; 70 mg, 35%). Isolation of
Isolation of the material forming the second green band afforded
4
2
3
Mo(CO)
2
(h
-(PPh
2
(o-C
6
H
4
)CH)
2
)(h
-C60) (3; 2 mg, 3%). MS (MALDI):
þ
98
þ
þ
m/z 1390 (M eCO, Mo), 1362 (M e2CO), 642 (M e2COeC60). IR
ꢀ1 1
ꢁ
(
CS , nCO): 1926s cm . H NMR (CDCl , 24 C): 7.83e6.99 (m, 24H,
2
3
3
.2.1. Compound 1
31
1
Ph), 4.30 (t, JPeH ¼ 6 Hz, 2H, CH]CH) ppm. P{ H} NMR (CD
2 2
Cl ,
4 2
Anal. Calc. for C40H30MoO P : C, 65.58; H, 4.13. Found: C, 65.18;
ꢁ
þ
98
24 C): 52.59 (s) ppm.
H, 4.43%. MS (FAB): m/z 734 (M , Mo), 734e28 n (n ¼ 1, 2). IR
ꢀ
1
1
ꢁ
(
(
2
CH
2
Cl
2
,
n
CO): 1976s, 1918s cm
.
H NMR (CD
2
Cl
2
, 22 C): 5.38
Cl
ꢁ
3
2 C): 18.04 (s) ppm. C{ H} NMR (CDCl , 24 C): 215.2 (dd,
31
1
3.5. Structure determination of 1 and 3
s, 2H, CHO), 7.69e6.93 (m, 28H, Ph) ppm. P{ H} NMR (CD
2
2
,
13
1
ꢁ
2
The crystals of 1 and 3 found suitable for X-ray analysis were
each mounted in a thin-walled glass capillary and aligned on the
J
PeC ¼ 17, 58 Hz, CO), 155.0e127.2 (Ph), 88.5 (s,
h -CHO) ppm.
Nonius Kappa CCD diffractometer, with graphite-monochromated
3
.2.2. Compound 2
Anal. Calc. for C24H18NMoO P: C, 56.38; H, 3.55; N, 2.74. Found: C,
4
6.56; H, 3.62; N, 2.73%. MS (MALDI): m/z 513 (M , Mo). IR
ꢀ
Mo K
a
radiation (
l
¼ 0.71073 A). The
q range for data collection is
þ
98
ꢁ
ꢁ
1.6e27.5 for 1 and 1.74e25.03 for 3. Of the 32,008 and 44,688
5
ꢀ
1 1
ꢁ
reflections collected for 1 and 3, 7652 and 11,560 reflections were
independent, respectively. All data were corrected for Lorentz and
polarization effects and for the effects of absorption. The structure
was solved by the direct method and refined by least-square cycles.
The non-hydrogen atoms were refined anisotropically. Hydrogen
atoms were included but not refined. All calculations were per-
formed using the SHELXTL-97 package [29]. The data collection and
refinement parameters are presented in Table 1.
(
(
{
2
J
CH
2 2
Cl ,
nCO): 2016s, 1903s, 1855s cm . H NMR (CDCl
3
, 24 C): 8.21
3
1
s, 1H, CH]N), 7.54e6.85 (m, 14H, Ph), 3.74 (s, 3H, NMe) ppm.
P
1
ꢁ
13
1
ꢁ
H} NMR (CDCl
21.0 (d, JPeC ¼ 8 Hz, CO), 216.6 (d, JPeC ¼ 33 Hz, CO), 207.8 (d,
PeC ¼ 9 Hz, CO), 168.5 (d, JPeC ¼ 3 Hz, CH ¼ N), 137.6 (d, JPeC ¼ 15 Hz,
), 134.4 (d, JPeC ¼ 7 Hz, C ), 133.5 (d, JPeC ¼ 14 Hz, o-C ),
33.1 (d, JPeC ¼ 33 Hz, ipso-C ), 131.9 (d, JPeC ¼ 25 Hz, C ), 131.7
),131.2 (s, C ),130.2 (s, p-C ),130.1 (s, C ),
), 61.7 (d, JPeC ¼ 2 Hz, CH ) ppm.
, 24 C): 36.27 (s) ppm. C{ H} NMR (CDCl , 24 C):
3 3
C
1
H
6 4
6
H
H
4
6 5
H
6
5
6 4
H
(
1
d, JPeC ¼ 4 Hz, C
H
6 4
6
H
4
H
6 5
6 4
H
28.7 (d, JPeC ¼ 15 Hz, m-C
6
H
5
3
Acknowledgements
3 3
3.3. Reaction of Mo(CO) (NCMe) and PCHO
This work was financially supported by the National Science
Council of Taiwan. We thank Mr. Ting-Shen Fuo (National Taiwan
Normal University, Taipei) and Mr. Gene-Hsiang Lee (National
Taiwan University, Taipei) for X-ray diffraction analysis.
Mo(CO)
3 3
(NCMe) (120 mg, 0.396 mmol) and PCHO (287 mg,
0
.99 mmol) were placed in an oven-dried 100 ml Schlenk flask
under a dinitrogen atmosphere. Dichloromethane (40 ml) was

1478
C.-S. Chen et al. / Journal of Organometallic Chemistry 696 (2011) 1474e1478
Appendix A. Supplementary material
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[
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