Reactions of cyclomanganated complexes with carbon disulfide: Routes to η2-aryldithiocarboxylate-Mn(CO)4 complexes and to the trithiocarbonate complex

Article abstract of DOI:10.1016/S0022-328X(02)02024-7

Reaction of cyclomanganated aryl ketones with CS₂ proceeds with insertion into the Mn-C bond to give η²- dithiocarboxylato-Mn(CO)₄ compounds. With other cyclomanganated substrates such as that from Ph₃P=S and al

Full text of DOI:10.1016/S0022-328X(02)02024-7

Journal of Organometallic Chemistry 664 (2002) 288ꢁ293
/
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Reactions of cyclomanganated complexes with carbon disulfide:
routes to h2-aryldithiocarboxylate-Mn(CO)4 complexes and to the
trithiocarbonate complex (m3-CS3)2Mn4(CO)16
Wade J. Mace, Lyndsay Main, Brian K. Nicholson ꢀ, Marion Hagyard
Department of Chemistry, University of Waikato, Private Bag 3105, Hamilton, New Zealand
Received 22 August 2002; accepted 29 September 2002
Abstract
Reaction of cyclomanganated aryl ketones with CS2 proceeds with insertion into the Mnꢁ
/
C bond to give h2-dithiocarboxylatoꢁ
S and also with Mn2(CO)10, CS2 gives (m3-
/
Mn(CO)4 compounds. With other cyclomanganated substrates such as that from Ph3PÄ
/
CS3)2Mn4(CO)16 with bridging trithiocarbonate ligands.
# 2002 Elsevier Science B.V. All rights reserved.
Keywords: Manganese; Cyclomanganates; Carbon disulfide; Insertion; Aryl dithiocarboxylate; Trithiocarbonate
1. Introduction
The MnꢁC bond of these species is a site of reactivity,
/
and combination with alkenes [6], alkynes [7], organoi-
socyanates [8], sulfur dioxide [9] or mercuric chloride
[10] have all been shown to generate novel derivatives.
For many of these reactions the first step in the process
There is now a well-developed chemistry of cyclo-
manganated complexes [1]. These compounds are read-
ily formed from aromatic and heteroaromatic ketones
[2], from substrates with imine or amine donor groups
[3], from triphenyl-phosphine or -arsine chalcogenides
[4], and from chalcones [5] to give, for example,
is undoubtedly insertion of the substrate into the MnꢁC
/
bond, followed by rearrangement with or without
demanganation.
compounds 1ꢁ3.
/
Another molecule that is known to insert into MꢁC
/
bonds (as well as into Mꢁ
/
H, Mꢁ
/
O, Mꢁ
/
P or MꢁS
/
bonds) is CS2 [11]. This generally leads to the formation
of bidentate dithiocarboxylate complexes (e.g.
ꢀ Corresponding author. Fax: ꢂ
E-mail address: b.nicholson@waikato.ac.nz (B.K. Nicholson).
/
64-7-838-4219
0022-328X/02/$ - see front matter # 2002 Elsevier Science B.V. All rights reserved.
PII: S 0 0 2 2 - 3 2 8 X ( 0 2 ) 0 2 0 2 4 - 7

W.J. Mace et al. / Journal of Organometallic Chemistry 664 (2002) 288ꢁ
/293
289
MeCS2Mn(CO)4 from MeMn(CO)5 [12]), although
monodentate species sometimes form (e.g.
2.3. Reactions
2.3.1. Reaction of h2-(2-acetyl-5-
methoxyphenyl)tetracarbonylmanganese with CS2
The cyclomanganated ketone 1 (133 mg, 0.42 mmol)
was placed in a thick-walled glass ampoule (ca. 20 ml
capacity). This was attached to a vacuum line, evac-
uated, and CS2 (ca. 10 ml) was distilled in. The ampoule
PtCl(SC(S)H)(PPh3)2 from Pt(H)(Cl)(PPh3)2 [13]. The
only previous investigation involving cyclometallated
substrates that we are aware of is the reaction of a nickel
complex to give, initially, a gem-dithiolate complex
which reacted further to give a h2-trithiocarbonate
complex and a thioketone (Eq. (1)) [14].
ð1Þ
We now report the reactions of CS2 with a range of
cyclomanganated complexes.
was sealed under vacuum and transferred to a Carius
tube where it was heated at 85 8C for 24 h. When the
cooled ampoule was stored at ꢃ20 8C for 72 h orange
/
crystals formed. The ampoule was opened and the
crystals were collected, and characterised as h2-(2-
acetyl-5-methoxyphenyldithiocarboxylato)tetracarbo-
nylmanganese, 4, (91 mg, 55%). M.p. 116 8C. Anal.
Found: C, 44.2; H, 2.3. Calc. for C14H9MnO6S2: C,
42.9; H, 2.3%. IR: n(CO) (CH2Cl2) 2093 (m), 2016 (vs),
2. Experimental
2.1. General
2002 (vs),1963 (s) cmꢃ1
;
1H-NMR: d 7.59 (1H, d,
8.6 Hz, H3), 7.02 (1H, dd, 3JHꢁH 8.5 Hz,
2.2 Hz, H4), 6.95 (1H, d, 4JHꢁH 2.1 Hz, H6),
All manipulations were carried out in an oxygen-free
N2 atmosphere with dried solvents in standard Schlenk
equipment or on a standard vacuum line. Orthomanga-
nated substrates were prepared by published methods
3JHꢁH
4JHꢁH
ꢄ
/
ꢄ
/
ꢄ
/
ꢄ
/
3.92 (3H, s, OCH3), 2.59 (3H, s, C(O)CH3). 13C-NMR:
d 199.2 (C7), 161.9 (C5), 149.2 (C1), 131.2 (C3), 129.6
(C2), 116.1 (C4), 113.0 (C6), 56.2 (OCH3), 29.6
(C(O)CH3); ESMS: (MeOH with added Na[OMe],
[2ꢁ5], while CS2 was purified by trap-to-trap distillation
/
on the vacuum line.
cone voltage 20 V), m/z 423 (33%) [Mꢂ
(100%) [MꢂOMeꢁ Hꢁ
CO]ꢃ; 363 (48%) [Mꢁ
(28%) [2Mꢁ
Mn(CO)5]ꢃ. This compound was also
/
OMe]ꢃ; 395
CO]ꢃ; 589
/
/
/
/
2.2. Instrumentation
/
characterised by an X-ray crystal structure determina-
tion; see below.
Infrared spectra were recorded on a Digilab FTS-40
FTIR spectrophotometer. NMR spectroscopy was per-
formed using a Bruker DRX400 Avance in CDCl3;
assignments were based on standard 2D experiments.
Routine electrospray mass spectra (ESMS) were ob-
tained on a VG Platform II spectrometer operating
under standard conditions in MeOH. Na[OMe] was
added as an ionisation aid [15]. Elemental analysis was
performed by the Campbell Microanalytical Labora-
tory, University of Otago. Melting points were mea-
2.3.2. Reaction of h2-(2-
benzoylphenyl)tetracarbonylmanganese with CS2
Cyclomanganated benzophenone (190 mg, 0.55
mmol) was reacted with CS2 (ca. 10 ml) in a sealed
ampoule at 85 8C for 24 h, following the same procedure
as above. The cooled ampoule was opened and the
excess CS2 removed under vacuum. The residue was
chromatographed on an alumina column, with diethyl
ether: petroleum spirits (1:1). The first fraction eluted
sured on a Reichart Thermopan melting point
apparatus and are uncorrected.

290
W.J. Mace et al. / Journal of Organometallic Chemistry 664 (2002) 288ꢁ293
/
gave a dark orange oil which did not crystallise. This
was characterised as h2-(2-benzoyl-phenyldithiocarbox-
ylato)tetracarbonylmanganese, 5, (156 mg, 67%). IR:
n(CO) (CH2Cl2) 2093 (m), 2019 (vs), 2007 (vs), 1964 (s)
2.3.5. Reaction of dimanganese decacarbonyl with CS2
Mn2(CO)10 (517 mg, 1.33 mmol) was reacted with CS2
in a sealed ampoule at 110 8C for 24 h. The unopened
ampoule was stored at ꢃ20 8C for 48 h, to give crystals
/
cmꢃ1; 1H-NMR: d 7.86ꢁ
196.9 (ꢁCOPh), 145.4 (C ꢁ
ESMS: (MeOH with added Na[OMe], cone voltage 10
V), m/z 455 (40%) [Mꢂ
OMe]ꢃ; 427 (100%) [Mꢂ
OMeꢁ
CO]ꢃ; 653 (78%) [2MꢁMn(CO)5]ꢃ.
/
7.43 (m, Arꢁ
/
H). 13C NMR: d
of the crude product. These were collected by filtration
and chromatographed on silica gel plates, eluting with
CH2Cl2:petroleum spirits (1:1) to give as the major
product (m3-CS3)2Mn4(CO)16, 7, (217 mg, 39%). Spec-
troscopic data was identical to that given in Section
2.3.4.
/
/
CS2), 137.6ꢁ
/
125.7 (other Ar);
/
/
/
/
2.3.3. Reaction of h2-(2-acetylthien-3-
yl)tetracarbonylmanganese with CS2
2.4. X-ray crystallography
The cyclomanganated thiophene derivative (112 mg,
0.38 mmol) was reacted with CS2 (ca. 10 ml) in a sealed
ampoule at 85 8C for 24 h, as above. Excess CS2 was
removed and the residue recrystallised from dichloro-
For compound 7 unit cell parameters and intensity
data were collected using a Siemens SMART CCD
diffractometer, using standard collection procedures,
˚
with monochromatic MoꢁKa X-rays (0.71073 A), while
/
methane: petroleum spirits at ꢃ20 8C. Dark yellow rods
/
of h2-(2-acetyl-thien-3-yl-dithiocarboxylato)tetracarbo-
nylmanganese, 6, were obtained (114 mg, 80%). M.p.
108 8C (dec.). Anal. Found: C, 36.1; H, 1.4. Calc. for
C11H5MnO5S3: C, 35.9; H, 1.4%. IR: n(CO) (CH2Cl2)
2093 (m), 2016 (vs, br),1966 (s) cmꢃ1; 1H NMR: d 7.45
for 4 a Siemens P4 four-circle diffractometer was used.
Corrections for absorption and other effects were
carried out with SADABS [16]. All other calculations
used the SHELX-97 programs [17]. The structures were
solved by direct methods, and developed routinely with
refinement based on F2. All non-hydrogen atoms were
assigned anisotropic temperature factors, and hydrogen
atoms were included in calculated positions.
3
3
(1H, d, JHꢁH
5.0 Hz, ArꢁH), 2.66 (3H, s, ꢁ
191.4 (ꢁC(O)CH3), 150.4 (Ar), 140.0 (Ar), 129.8 (Arꢁ
H), 128.4 (ArꢁH), 30.0 (ꢁC(O)CH3). ESMS: (MeOH
with added Na[OMe], cone voltage 10 V), m/z 399
(68%) [Mꢂ OMeꢁ
OMe]ꢃ; 371 (74%) [Mꢂ CO]ꢃ; 339,
(16%) [MꢁCOꢁ
H]ꢃ; 541 (100%) [2MꢁMn(CO)5]ꢃ.
ꢄ
/
5.0 Hz, Arꢁ
/
H), 7.24 (1H, d, JHꢁH
ꢄ
/
/
/
C(O)CH3). 13C NMR: d
/
/
/
/
2.4.1. Crystal data for h2-(2-acetyl-5-methoxyphenyl-
dithiocarboxylato)tetracarbonylmanganese (4)
/
/
/
/
/
/
C14H9MnO6S2, Mr 392.27, orthorhombic, Pnma, aꢄ
/
˚
22.878(8), bꢄ
/
7.005(3), cꢄ
1.630 g cmꢃ3, Zꢄ
Ka) 1.113 mmꢃ1, Tmax 0.262, Tmin 0.238, crystal size
0.66ꢅ0.17ꢅ
0.04 mm3. T 168 K.
A total of 1999 reflections, 1364 unique (Rint 0.0407)
was collected 2Bu B248. Final R1 0.0415 [data with
I ꢀ2s(I)], 0.0767 (all data), wR2 0.0863, GoF 1.014,
final De ꢂ0.37/ꢃ0.35.
/
9.973(6) A, Vꢄ
/
1598.1(14)
3
˚
2.3.4. Reaction of h2-[(2-diphenylthiophosphinyl)-
phenyl]tetracarbonylmanganese with CS2
A , Dcalc
ꢄ
/
/
4, F(000)ꢄ792, m(Moꢁ
/
/
/
/
Cyclomanganated triphenylphosphine sulfide (2b)
(125 mg, 0.31 mmol) was reacted with CS2 as above.
31P-NMR and ESMS on the crude reaction mixture
showed the presence of the starting material 2b and
Ph3PS. Excess CS2 was removed and the residue
/
/
/
/
/
The structure is illustrated in Fig. 1, while selected
recrystallised from CH2Cl2: Et2O at ꢃ
yield of orange blocks were obtained, identified as (m3-
CS3)2Mn4(CO)16 (7). M.p.ꢀ115 8C (dec.). Anal.
/
20 8C. A small
bond parameters are listed in the caption.
/
Found: C, 23.5; H, 0.0. Calc. for C18Mn4O16S6: C,
24.5; H, 0.0%. IR: n(CO) (CH2Cl2) 2091 (s), 2049 (m),
2009 (vs, br), 1979 (m), 1965 (m) cmꢃ1; ESMS: (MeCN,
2.4.2. Crystal data for (m3-CS3)2Mn4(CO)16 (7)
¯
C18Mn4O16S6, Mr 884.30, triclinic, P1, aꢄ
/
7.010(3),
cone voltage 10 V), m/z 717 (100%) [Mꢁ
689 (27%) [MꢁMn(CO)4ꢁ
CO]ꢃ; 661, (8%) [Mꢁ
Mn(CO)4ꢁ
2CO]ꢃ. The characterisation was confirmed
/
Mn(CO)4]ꢃ;
bꢄ
gꢄ
Zꢄ
1.00, Tmin 0.76, crystal size 0.26ꢅ
168 K.
A total of 9436 reflections, 3016 unique (Rint 0.0333)
was collected 2Bu B26.58. Final R1 0.0309 [data with
I ꢀ2s(I)], wR2 0.0702, GoF 0.954, final De ꢂ0.63/ꢃ
/
8.410(4), cꢄ
/
13.674(6) A, aꢄ
/
83.40(1), bꢄ
/
80.04(1),
˚
3
ꢄ ,
1.927 g cmꢃ3
/
˚
/
/
/
/
74.21(1)8, Vꢄ
/
762.1(5) A , Dcalc
432, m(Moꢁ
/
/
1, F(000)ꢄ
/
/
Ka) 2.099 mmꢃ1, Tmax
0.16ꢅ
0.05 mm3. T
by an X-ray crystal structure analysis; see below.
Similar reactions of orthomanganated triphenylpho-
sphine selenide (2c), orthomanganated triphenylpho-
sphine phenylimine (2a) and the orthomanganted
chalcone (3a), also gave low yields of (m3-
CS3)2Mn4(CO)16 as the only carbonyl-containing pro-
duct.
/
/
/
/
/
/
/
0.50. The structure is illustrated in Fig. 2, with selected
bond parameters in the caption.

W.J. Mace et al. / Journal of Organometallic Chemistry 664 (2002) 288ꢁ
/293
291
Fig. 1. The structure of h2-(2-acetyl-5-methoxyphenyldithiocarboxylato)tetracarbonylmanganese (4). Bond parameters include: Mn(1)ꢁ
/
S(1)
˚
2.381(1), S(1)ꢁ
/
C(1) 1.676(3), Mn(1)ꢁ
/
C(11) 1.815(5), Mn(1)ꢁ
/
C(12) 1.869(7) A; S(1)ꢁ
/
Mn(1)ꢁ
/
S(1?) 72.73(6)8, Mn(1)ꢁ
/
S(1)ꢁ
/
C(1) 86.2(2)8, S(1)ꢁ
/
C(1)ꢁS(1?) 114.7(3)8.
/
3. Results and discussion
NMR spectra were consistent with the dithiocarboxylate
structure. Similarly the electrospray mass spectrum,
with Na[OMe] added as an ionisation aid [15], gave
expected peaks arising from both OMeꢃ addition and
Hꢂ abstraction from 4. However, the spectroscopic
data did not completely distinguish between the h2-
RCS2 bonding pattern as in 4, and an alternative which
The reaction of the cyclometallated acetophenone 1
with CS2 at 85 8C for 24 h gave a reasonable yield of the
dithiocarboxylate complex (h2-MeOC6H4CS2)Mn(CO)4
(4), which crystallised on cooling the reaction mixture.
The temperature of reaction was critical; below 80 8C
little change took place while above 90 8C extensive
decomposition occurred.
The new complex 4 showed in the IR spectrum a
characteristic nCO pattern for a cis-L2Mn(CO)4 species,
with a shift of around 10 cmꢃ1 to higher frequencies
compared with the starting complex 1. The 1H- and 13C-
has an h1-RCS2 with the ÈCÄ
/O of the acetyl group still
coordinated, as in 8. Therefore, a single crystal X-ray
determination was carried out to distinguish between the
two possibilities.
The structure is illustrated in Fig. 1. It shows that
structure 4 is adopted, with the Mn(CO)4 group
attached to the organic ligand by a symmetrical h2-
RCS2 linkage. The CS2 group is orthogonal to the aryl
plane of the rest of the ligand, and the CÄ
/
O group is
uncoordinated. As expected, the MnꢁCO distances of
/
the two CO ligands trans to each other are significantly
longer than the Mn-CO bonds trans to the dithiocar-
boxylate ligand.
The corresponding reactions of orthomanganated
benzophenone, and the orthomanganated 2-acetylthio-
phene complex, with CS2 under the same conditions
produced the equivalent dithiocarboxylate complexes 5
and 6 respectively. This suggests that for manganated
aryl ketones the conversion of the C,O-bonded R ligand
to a RCS2 ligand is general.
A suggested pathway to 4ꢁ
involves initial insertion of CS2 into the Mnꢁ
/
6 in these reactions
C bond
/
to give a S,O-bonded ligand with a seven-membered
chelate ring, as in 8. Displacement of the O-donor by the
second sulfur atom would give the final product. This
pathway is consistent with reactions of orthomanga-
nated complexes involving other unsaturated molecules.
Fig. 2. The structure of (m3-CS3)2Mn4(CO)16 (7). Bond parameters
include: Mn(1)ꢁ
/
S(1) 2.3866(11), Mn(1)ꢁ
S(1) 1.691(3), C(1)ꢁ
1.763(3) A; S(1)ꢁMn(1)ꢁS(2) 73.18(3)8, Mn(2)ꢁ
100.18(3)8, S(3)ꢁMn(2)ꢁS(3?) 79.82(3)8, Mn(1)ꢁ
86.41(10)8, S(1)ꢁC(1)ꢁS(2) 114.52(16)8, S(1)ꢁC(1)ꢁS(3) 122.84(16),
S(2)ꢁC(1)ꢁS(3) 122.53(16)8. The inset is a side view emphasising the Z-
shape of the molecule.
/
S(2) 2.3971(13), Mn(2)ꢁ
S(2) 1.699(3), C(1)ꢁS(3),
S(3)ꢁMn(2?)
S(1)ꢁC(1)
/
S(3)
2.4035(13), C(1)ꢁ
/
/
/
˚
/
/
/
/
Although compounds 4ꢁ6 are new examples, other
/
/
/
/
/
dithiocarboxylate complexes of Mn(CO)4 are estab-
lished, having been prepared previously by insertion of
/
/
/
/
/
/
CS2 into the MnꢁC bond of RMn(CO)5 compounds
/

292
W.J. Mace et al. / Journal of Organometallic Chemistry 664 (2002) 288ꢁ293
/
[12]. This earlier method, however, gave much lower
yields (1ꢁ17%) than those found in the present study for
the cyclomanganated substrates (55ꢁ80%). There ap-
pear to be only two instances of the direct reaction of
dithiocarboxylate anions with either BrMn(CO)5 or
[Mn(CO)5(MeCN)]ꢂ to give related species [18]. There-
fore the reaction of CS2 with orthomanganated aryl
ketones may provide a useful route to dithiocarbox-
ylates, especially those with functional groups that
would interfere with the other syntheses.
Compound 7 does not appear to have been reported
before, but the isomorphous Re analogue was isolated
from the reaction of F3CRe(CO)5 with CS2 [12,22].
The route to 7 is not clear. It seemed possible that the
third S atom might have come from the orthomanga-
/
/
nated Ph3PÄ
the product (albeit in low yield) when using the
corresponding orthomanganated Ph3PÄSe (2c); ESMS
/S, but this was discounted when 7 was also
/
of the crude reaction mixture showed no traces of a
dithioselenocarbonate analogue of 7 which would have
been expected if atom transfer from the phosphine
chalcogenide was involved.
The reaction of CS2 with orthomanganated triphenyl
phosphine sulfide, 2b, was also investigated. This gave
no evidence for the formation of a dithiocarboxylate,
with the only new carbonyl-containing product being
dark-yellow crystals isolated in low yield. Spectroscopic
and analytical data were inconclusive, so an X-ray
structure determination was carried out. This showed
the product to be 7 as illustrated in Fig. 2. The
centrosymmetric molecule consists of two h3-trithiocar-
bonate anions, each with two of the sulfur atoms
chelating to a Mn(CO)4 group, while the third acts as
a bridging atom between two other Mn(CO)4 groups.
Similarly Ph3PÄ/NPh (2a) and chalcone (3) gave low
yields of 7 when they were reacted with CS2 under the
same conditions.
To find a more rational synthesis of 7, Mn2(CO)10
was reacted with CS2. Although a higher temperature
was needed (110 8C) the isolated yield of 7 was reason-
able, 39%. It seems that formation of CS23ꢃ ligands can
readily arise from a formal redox disproportionation of
CS2 in reactions of a variety of manganese [21] (or
rhenium [22] or nickel [14]) compounds.
The CS23ꢃ groups are planar, with shorter Cꢁ
/
S bonds to
˚
the chelating S atoms (1.695 A) than to the bridging one
˚
(1.763 A). The pyramidality at the bridging S atom
induces a Z shape to the molecule (see inset to Fig. 2).
The overall molecule is a combination of two common
4. Supplementary material
motifs *
(h2-RCS2)Mn(CO)4 as in the dithiocarbox-
/
Crystallographic data for the structural analysis have
been deposited with the Cambridge Crystallographic
Data Centre, CCDC nos. 194981 and 194982 for
compounds 4 and 7, respectively. Copies of this
information may be obtained free of charge from The
Director, CCDC, 12 Union Road, Cambridge CB2 1EZ,
ylates discussed above [12,18] and related species [19],
and a (m-SR)2Mn2(CO)8 unit which is well-known for
manganese carbonyl thiolates [20].
Also related to compound 7 are the [(h2-CS3)-
Mn(CO)4]ꢃ and (CO)5Mn(h3-CS3)Mn(CO)4 complexes
found by Benson et al in reactions of [Mn(CO)5]ꢃ with
CS2 [21].
UK (Fax: ꢂ
/
44-1223-336033; e-mail: deposit@ccdc.
cam.ac.uk or www: http://www.ccdc.cam.ac.uk).

W.J. Mace et al. / Journal of Organometallic Chemistry 664 (2002) 288ꢁ
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293
(d) W. Tully, L. Main, B.K. Nicholson, J. Organometal. Chem.
503 (1995) 75;
Acknowledgements
(e) W.J. Grigsby, L. Main, B.K. Nicholson, J. Organometal.
Chem. 540 (1997) 185.
We thank the University of Waikato for financial
support and for a postgraduate scholarship (W.M.). We
thank Associate Professor C.E.F. Rickard, University of
Auckland, and Professor W.T. Robinson, University of
Canterbury, for X-ray data sets.
[7] (a) L.S. Liebeskind, J.R. Gasdaska, J.S. McCallum, S.J. Tremont,
J. Org. Chem. 54 (1989) 669;
(b) N.P. Robinson, L. Main, B.K. Nicholson, J. Organometal.
Chem. 364 (1989) C37;
(c) R.C. Cambie, M.R. Metzler, P.S. Rutledge, P.D. Woodgate, J.
Organometal. Chem. 429 (1992) 41;
(d) W.J. Grigsby, L. Main, B.K. Nicholson, Organometallics 12
(1993) 397;
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