Transition Metal Chemistry (2018) 43:549–554

https://doi.org/10.1007/s11243-018-0238-0

Kinetics and mechanism of pyridine substitution

from [(η3‑C3H5)Mo(CO)2(X)(py)2] (X = Cl, Br; py = pyridine)
by 1,2‑bis(diphenylphosphino)ethane
Khalil J. Asali1 · Mohammad El‑khateeb1 · Wolfgang Weigand2

Received: 26 March 2018 / Accepted: 20 April 2018 / Published online: 3 May 2018
© Springer International Publishing AG, part of Springer Nature 2018

Abstract
Reactions of [(η3-C3H5)Mo(CO)2(X)(py)2] (X = Cl (1), Br (2); py = pyridine) with 1,2-bis(diphenylphosphino)ethane (= dppe)
in toluene solution resulted in replacement of the py ligands and the formation of [(η3-C3H5)Mo(CO)2(X)(κ2-P,Pʹ-dppe)].
Thermal kinetics of these substitution reactions, under pseudo-first-order reaction conditions, indicated that these reactions
proceed by a rate law that is first order in the concentration of the metal complex and zero order in dppe concentration. The
data suggest a two-step substitution process. The first step is slow and reversible, involving the dissociation of the first py
coligand to form a coordinatively unsaturated [(η3-C3H5)Mo(CO)2(X)(py)] transient species. This is followed by an irrevers-
ible end-on coordination of the dppe ligand at the transient species to give [(η3-C3H5)Mo(CO)2(X)(py)(κ1-P-dppe)] as an
intermediate. The latter complex undergoes a fast and entropy-driven ring closure, resulting in the substitution of the second
py ligand to give [(η3-C3H5)Mo(CO)2(X)(κ2-P,Pʹ-dppe)]. Rate constants and activation parameters for these reactions have
been determined and discussed. Competition studies for the [(η3-C3H5)Mo(CO)2(X)(py)] intermediates show that these
transients are highly reactive and react almost indiscriminately with both py and dppe.

Introduction (phen), 2,2′-bipyridine (bipy)) [13, 14] or bidentate P-donor

Research on late group 6 metal carbonyl complexes contain-
ing mixed η3-allyl/dicarbonyl ligands has received increasing
attention over the past few decades due to their application
in several catalytic organic processes such as symmetric and
asymmetric allylic alkylation [1–9], olefin epoxidation [10],
polymerization [11], and oligomerization reactions [12]. A
large number of such complexes have been prepared and
characterized by the reaction of the precursor [(η3-C3H5)
M(CO)2(CH3CN)2X)] (X = Cl, Br; M = Mo, W) with various
bidentate N-donor chelating ligands (1,10-phenanthroline
* Khalil J. Asali
* Mohammad El‑khateeb
kateeb@just.edu.jo
1 cis-Mo(CO)4(py)2 in THF solution to generate initially [(η3-
Chemistry Department, Jordan University of Science
and Technology, Irbid 22110, Jordan
2 afford [(η3-allyl)(η5-Cp)Mo(CO)2] [20].
Institut für Anorganische und Analytische Chemie,
Friedrich-Schiller-Universität Jena, Humboldt Str. 8,
07743 Jena, Germany
bis(phosphines) (= dppa) [15, 16]. Despite the extensive
interest in these complexes, most studies in this area have
focused on the structural aspects, the dynamic behavior and
isomerism in solution at various temperatures, especially
for [(η3-allyl)M(CO)2(dppa)(X)] [16], and the reactivity of
different precursors which are used to obtain the target M(η3-
allyl)(CO)2 containing complexes [17, 18].
Different reagents have been employed for the prepara-
tion of Mo(II) complexes containing allylic moieties. For
example, allyl halides react with Mo(CO)3(CH3CN)3, in
an oxidative addition-type reaction, to afford [(η3-C3H5)
Mo(CO)2(CH3CN)2(X)] [13, 14]. Pearson et al. [19] reported
that Mo(CO)3(py)3 is a convenient reagent for the synthesis
of a variety of allylic substrates including halides and ace-
tates containing (η3-allyl)Mo(II) fragments. However, Kuhl
et al. demonstrated that cis-Mo(CO)4(py)2 is a superior start-
ing reagent for the synthesis of allyl/Cp mixed complexes.
For example, allyl acetates or allyl esters oxidatively add to
allyl)M(CO)2(py)2(OAc)], which reacts in situ with LiCp to
To the best of our knowledge, thermal kinetic studies
which describe the mechanism of oxidative addition of

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550
allyl halides or pseudo-halides to group 6 metal carbonyl
complexes or the replacement of one or more labile ligands
from the commonly used precursors such as [(η 3-C3H5)
M(CO)2(L)2(X)] (L = CH3CN, THF, py; X = halide, pseudo
halide) are scarce and remain unexplored [21]. In this inves-
tigation, we wish to report the thermal kinetics and the acti-
vation parameters associated with pyridine displacement
from [(η3-C3H5)M(CO)2(py)2(X)] (X = Br, Cl) by dppe in
toluene solution.
Experimental
Materials and methods
All reactions were performed using Schlenk line techniques
under a ­N2 atmosphere. Toluene, dichloromethane (dried
over ­P2O 5), hexane, and THF (Na/benzophenone) were
dried and distilled prior to use. Mo(CO)6 (Aldrich) was
used as received. Allyl chloride and allyl bromide (Aldrich)
were distilled and kept under an inert atmosphere. The
dppe proligand was recrystallized from absolute ethanol.
Pyridine was fractionally distilled from KOH. The com-
plexes cis-M(CO)4(py)2 were prepared by reported meth-
ods [20].
The UV–Vis data were collected using a Shimadzu instru-
ment. Infrared spectra were recorded with Bruker Equinox 55
and Nicolet Impact 410 FT-IR spectrometers. Elemental analy-
sis was performed with a Leco CHNS-932 apparatus.
Preparation of the complexes
[(η3‑C3H5)Mo(CO)2(X)(py)2] (X = Cl (1), Br (2))
A mixture of cis-M(CO)4(py)2 (8.2 mmol) and slight excess of
the allyl halide (9.0 mmol) in 80 cm3 of dry THF was heated
to reflux with stirring under a N
­ 2 atmosphere for about 12 h.
The reaction was then cooled to room temperature and filtered
over Celite. The volatiles were removed under vacuum. The
resulting yellow residue was collected and recrystallized from
THF/hexane (1:3 v:v) at about −5 ºC.
[(η 3 -C 3 H 5 )Mo(CO) 2 (Cl)(py) 2 ] (1): Yield = 92%.
M.p = 160–163 °C (dec.). Anal. calc. for ­C15H15N2O2ClMo
(%): C, 46.59; H, 3.91; N, 7.24. Found: C, 46.78; H, 3.82; N,
7.49. IR ­(CH2Cl2) ­(cm−1): 1935 (s) vco; 1848 (s) vco.
[(η 3 -C 3 H 5 )Mo(CO) 2 (Br)(py) 2 ] (2): Yield = 84%.
M.p = 148–150 °C (dec.). Anal. calc. for C ­ 15H15N2O2BrMo
(%): C, 41.79; H, 3.51; N, 6.50. Found: C, 41.58; H, 3.42; N,
6.62. IR ­(CH2Cl2) ­(cm−1): 1931 (s) vco; 1849 (s) vco.
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Transition Metal Chemistry (2018) 43:549–554
[(η3‑C3H5)Mo(CO)2(dppe)(X)] (X = Cl (3), Br (4))
These complexes were prepared by a slightly modified pro-
cedure to the one reported in the literature [16].
A mixture of [(η3-C3H5)Mo(CO)2(X)(py)2] (5.0 mmol)
and slight excess of the dppe ligand (5.2 mmol) in toluene
(~ 80 cm3) were allowed to react under a N ­ 2 atmosphere
at ~ 50 °C for 8 h with stirring. The color of the reaction
mixture changed from bright yellow to orange red. The solu-
tion was regularly checked with TLC during the course of
the reaction. On completion, the resulting solution was fil-
tered while hot over Celite. The product precipitated as an
orange-red solid by addition of about 50 cm3 of hexane at
ambient temperature and was collected by suction filtration.
Recrystallization from ­CH2Cl2/hexane (1:2 v:v) (~ − 5 °C)
gave the analytically pure samples.
[(η 3 -C 3 H 5 )Mo(CO) 2 (dppe)(Cl)] (3): Yield = 90%.
M.p = 208–210 °C (dec.). Anal. calc. for C ­ 31H29O2ClP2Mo
(%): C, 59.39; H, 4.66. Found: C, 59.14; H 4.52. IR (­ CH2Cl2)
­(cm−1): 1940 (s) vco; 1846 (s) vco.
[(η 3 -C 3 H 5 )Mo(CO) 2 (dppe)(Br)] (4): Yield = 82%.
M.p = 186–189 °C (dec.). Anal. calc. for C ­ 31H29O2BrP2Mo
(%): C, 55.46; H, 4.35. Found: C, 55.30; H, 4.36. IR
­(CH2Cl2) ­(cm−1): 1942 (s) vco; 1848 (s) vco.
Thermal kinetic measurements
Thermal kinetic studies were carried out in quartz screw-
capped cells under nitrogen at constant temperature (± 0.1 °C)
which was maintained using a thermostated bath. The kinetic
data were collected spectrophotometrically by follow-
ing the disappearance of the reactants’ absorption band (1:
λ = 410 nm, 2: λ = 420 nm). The kinetic runs were carried
out under pseudo-first-order conditions by employing a large
excess of concentration of the incoming dppe ligand (25-fold
or more) over that of the complexes 1 or 2 (~ 5.0 × 10−5 M) in
toluene solution. The progress of the reactions was followed
for four or more half-lives, and the reaction was kept in pro-
gress until A∞ has practically been reached (> 90% comple-
tion). Rate constants were evaluated by a linear least-squares
fitting program using the first-order rate equation:
( ) ( )
ln At − A∞ = − k.t + ln A0 − A∞
where At, A0, and A∞ are the absorbance at time t, initial
absorbance, and the absorbance at infinite time, respectively.
The activation parameters ΔHǂ and ΔSǂ were determined
from the values of rate constants at different temperatures
by employing the Eyring equation and were analyzed using
a linear least-squares fitting program. Data were rejected
at 90% confidence limit. The limits of error (uncertainty of
the last digit(s)) are one standard deviation and are given in
parentheses.
Transition Metal Chemistry (2018) 43:549–554
Results and discussion
The complexes 3 and 4 were obtained in good yields as
orange-red solids by the reactions of the precursor [(η 3-
C3H5)Mo(CO)2(X)(py)2] (X = Cl, Br) with dppe in toluene
solution. They have been characterized by elemental analy-
sis and IR spectroscopic data. The physical properties of
these complexes were in good agreement with those reported
by Faller et al. [16]. The carbonyl stretching frequencies
in these complexes exhibited two bands of almost equal
intensity ­(A1 + B1) as expected for two cis-carbonyls under
­C2v local symmetry. Complexes 3 and 4 are air stable, solu-
ble in most polar or slightly polar solvents such as THF,
­CH2Cl2, toluene but insoluble in nonpolar solvents such as
hexane and other hydrocarbons. The dynamic nature of these
complexes in solution (fluxionality and stereochemistry)
was investigated by Faller et al. [16] and has been recently
reviewed by Ryan et al. [17].
Thermal kinetics of replacement of py by dppe
from complexes 1 and 2
The thermal kinetics of py replacement during the reac-
tions of the complexes 1 or 2 were conducted in the pres-
ence of 25-fold or more excess of the concentration of dppe
(0.00125–0.00942 M) to ensure pseudo-first-order reaction
conditions in toluene solution (Eq. 1).
(1)
Plots of ln(At − A ∞) versus time exhibited a linear
relationship to more than 90% completion. Values of the
pseudo-first-order rate constants, k obs, were determined
from the slopes of these plots and are collected in Table 1.
The data indicates that, at a given temperature, the values
of kobs are independent of the concentration of the entering
dppe and thus vary linearly only with the concentration
of the metal complexes. That the obtained rate constants
which were determined from the slopes of the plots as the
reaction approaches t∞ are the same as those near t0 and
that no detectable curvature in the plots was observed,
551
indicates that a single step is rate-limiting. A mechanism
for this observation can be envisaged as a reversible disso-
ciation of the first py ligand to generate the coordinatively
unsaturated [η3-C3H5)Mo(CO)2(X)(py)] transient species,
followed by rapid attack of end-on coordination of the
dppe ligand to afford the complex [η3-C3H5)Mo(CO)2(X)
(py)(κ1-P-dppe)]. The latter complex undergoes fast ring
closure with extrusion of the second py ligand to afford
[η3-C3H5)Mo(CO)2(X)(κ2-P,Pʹ-dppe)]. Several examples
of fast ring closure in complexes containing P-donor
or N-donor bidentate ligands of the type M-(κ1-P-P) or
M-(κ1-N-N) to form the chelated ones are known in the
literature [22–25]. We have previously reported a rapid
ring closure of a solvated [Mo(CO)4(κ1-P-dppe)(toluene)]
transient species, which was generated photochemically by
pulsed laser flash photolysis of Mo(CO) 4(dppe) in tolu-
ene. This occurs rapidly and is much faster than attack by
L (L = phosphine, phosphite) to re-form Mo(CO) 4(dppe)
[22]. Moreover, the rapid coordination of dppe on Mo
carbonyl complexes followed by rapid ring closure was
also observed for the reactions of dppe with cis-[Pt(CO)
(Ph) 2 (SEt 2 )], which initially gave [Pt(CO)(Ph) 2 (κ 1 -P-
dppe)] followed by fast CO release to give [Pt(Ph)2(κ 2-
P,Pʹ-dppe)] [23]. Unfortunately, all attempts to isolate the
complex [η3-C3H5)Mo(CO)2(X)(py)(κ1-P-dppe)] in pure
form by thermal methods were unsuccessful and thus pre-
cluded a separate thermal kinetic study of ring closure in
these complexes.
The rate law for py replacement from complexes 1 or 2
can be derived by assuming the steady-state approxima-
tion in the concentration of the initially formed [(η3-C3H5)
Mo(CO)2(X)(py)] intermediate. Thus if M represents the
two Mo carbonyl complexes (1, 2),
[ ] [ ] [ ]
Rate = − d[M]∕dt = k1 k2 [M] dppe ∕(k−1 py ) + k2 dppe ),
(2)
(3)
[ ] [ ] [ ]
kobs = k1 k2 dppe ∕(k−1 py + k2 dppe ).
Under pseudo-first-order reaction conditions,
k2[dppe] ≫ k−1[py], thus:
Rate = kobs [M] where kobs = k1 (4)
Values of the first-order rate constants for initial Mo-py
dissociation from [(η3-C3H5)Mo(CO)2(X)(py)2] indicate
that the reaction is faster when X = Cl (1) compared to that
when X = Br (2). This could be due to less electron density
at Mo of complex 1 resulting in a weaker Mo–N bond and
is in agreement with several reports confirming this trend
by employing various spectroscopic and structure deter-
mination techniques [13, 14, 26–28].
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552 Transition Metal Chemistry (2018) 43:549–554

Table 1  Rate constants and X T (± 0.1) °C) [dppe], M 104kobs ­(s−1) ΔHǂ (kcal/mol) ΔSǂ (cal/mol K)
activation parameters for
the thermal reactions of Cl 25.0 0.00125 1.28 (6) 28.4 (7) 20.0 (8)
[Mo(CO)2(η3-C3H5)(X)(py)2]
0.00325 1.26 (3)
with dppe in toluene at various
temperatures 0.00822 1.21 (5)
35.0 0.00125 5.70 (8)
0.00440 5.55 (4)
0.00682 5.62 (2)
45.0 0.00320 27.3 (8)
0.00645 26.9 (5)
0.00885 27.4 (5)
Br 25.0 0.00120 0.922 (4) 27.5 (6) 16.4 (5)
0.00425 0.932 (6)
0.00910 0.916 (7)
35.0 0.00140 4.15 (6)
0.00504 4.09 (5)
0.00882 4.27 (9)
45.0 0.00120 18.1 (5)
0.00645 18.4 (4)
0.00942 18.2 (3)

Competition for the [(η3‑C3H5)Mo(CO)2(X)(py)]

25
intermediates Br
20 Cl R² = 0.9996
Competition studies for the [(η3-C3H5)Mo(CO)2(X)(py)]
10-3 1/kobs (s)

intermediates were conducted by using excess of both py 15

(concentration range 0.000338–0.00180 M) and dppe (con- R² = 0.9968

centration range 0.00124–0.00645 M) simultaneously in 10

toluene solution (~ 5.0 × 10−5 M in metal complex). Values
of A∞ in these reactions were tested and found to be around 5
8–10% of the original absorbance, A0, which is within the
acceptable limits of error in these measurements. This obser- 0
0.0 0.2 0.4 0.6 0.8 1.0 1.2 1.4 1.6
vation confirms that the reaction (Eq. 1) proceeds to com-
[Py]/[DPPE]
pletion, but at slower rates, in the presence of additional
pyridine (up to 1.80–10−3 M) and excess dppe. In this case,
Fig. 1  Plots of 1/kobs versus the concentration ratio [py]/[dppe] for
Eq. 3 can be rearranged to Eq. 5,
reactions of [(η3-C3H5)Mo(CO)2(X)(py)2]) (X = Cl (1), Br (2)) with
dppe and py in toluene at 25 °C
(5)
[ ]
1∕kobs = 1∕k1 + k−1 py ∕k1 k2 [dppe].
Plots of 1/kobs versus [py]/[dppe] ratios are expected to be
linear, with slopes = k−1/k1k2 and an intercept = 1/k1. Taking five-coordinate intermediates [M(CO)4(EPh3)] (M = Mo, W;
into consideration that values of k1 are independent of the E = As, Sb) [29]. The values of k1 determined in the absence
concentration of the entering dppe ligand, the competition of added py and those obtained from the reciprocal of the
ratios k2/k−1, which describe the reactivity of dppe compared intercepts of the above-mentioned plots are comparable within
to py, can be evaluated from the intercept/slope ratios of these experimental error. This observation supports the validity of
plots, as shown in Fig. 1 and Table 2. Competition ratios the proposed mechanism as given in Scheme 1 (vide supra).
(1.42 for complex 1 and 1.21 for complex 2) indicate that
the [(η3-C3H5)Mo(CO)2(X)(py)] intermediates react with the Activation parameters
incoming nucleophiles almost indiscriminately, with a slight
preference for reaction with dppe compared to py. This obser- The activation parameters ΔΗǂ and ΔSǂ for reactions of
vation is in good agreement with our recently reported data complexes 1 and 2 with dppe were obtained from the plots
for similar competitive reactions of some tertiary phosphine of ln(k/T) versus 1/T (Fig. 2). Enthalpies of activation,
monodentate ligands such as P ­ Ph3 or (tBu)3P and py for the ΔΗǂ, determined through this study are very close to each

13
Transition Metal Chemistry (2018) 43:549–554 553

Table 2  First-order rate constants and competition ratios for the ther-
mal reactions of the complexes [(η3-C3H5)(Mo(CO)2(X)(py)2] with -11.5 Br
dppe and py in toluene at 25 °C Cl
-12.5
X [Py]/[dppe] 105k1 ­(s−1) Competition R² = 0.9998

ln (k/T)
ratio = k2/k−1
-13.5

Cl 0.00 12.5 (6) 1.42 (3) R² = 0.9987

0.0522 12.0 (3) -14.5

0.108 11.5 (8)

-15.5
0.194 11.2 (9) 0.0031 0.00315 0.0032 0.00325 0.0033 0.00335 0.0034
0.325 10.0 (4) 1/T (K-1)
0.558 8.95 (6)
0.772 8.31 (5) Fig. 2  Plots of ln(k/T) versus 1/T for the reaction of [(η3-C3H5)
0.965 7.41 (5) Mo(CO)2(X)(py)2]) (X = Cl (1), Br (2)) with dppe in toluene at vari-
1.22 6.78 (2) ous temperatures
1.45 6.14 (6)
Br 0.00 9.20 (4) 1.21 (2)
0.0265 9.00 (2) Conclusion
0.0625 8.75 (4)
0.0888 8.60 (8) A thermal kinetic study of py displacement from [(η3-C3H5)
0.135 8.28 (2) Mo(CO)2(X)(py)2] (X = Cl, Br) by dppe was undertaken. The
0.305 7.35 (5) results suggested that these reactions proceed by a rate law
0.525 6.42 (3) that is first order in the concentration of the metal complex
0.622 6.10 (7) and zero order in dppe concentration. Substitution of py from
0.861 5.38 (3) these complexes proceeds via an initial (slow and reversible)
1.02 4.98 (6) Mo-py bond breaking as rate-controlling step followed by
other fast steps which involve rapid dppe ring closure with
substitution of the second py to give the final reaction product.
other (28.4 and 27.5 kcal/mol for complex 1 and complex The rate constants and the activation parameters, ΔΗǂ and
2, respectively). These values, most probably, reflect the ΔSǂ, for these reactions have been determined.
upper limit of Mo(II)-py bond energies in these complexes
and are ca. 4–5 kcal/mole higher than Mo(0)-py bond ener- Acknowledgements This research was funded by the Deanship of
gies in complexes which react via initial Mo-py bond fission Research at Jordan University of Science and Technology, under Grant
No. (56/2016). K.J. Asali thanks Jordan University of Science and
[22, 25, 29]. Moreover, the obtained entropies of activation, Technology for a sabbatical leave.
ΔSǂ, associated with k1 are positive and are consistent with
a dissociative mechanism which reflects an increase in dis-
order while attaining the transition state during Mo-py bond
breaking [22, 25].

X = Cl, Br; py = pyridine; P-P = dppe

Scheme 1  Proposed mechanism for py substitution from complexes 1 and 2 by dppe

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554 Transition Metal Chemistry (2018) 43:549–554

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