Synthesis and characterization of η3-Allyl palladium(II) complexes with tetraalkyldiphosphine disulfides, R2P(S)P(S)R 2 (R=Me, Et, nPr, nBu, Ph)

Article abstract of DOI:10.1080/15533174.2011.591311

New allyl-palladium tetraalkyl(phenyl)diphosphine disulfide complexes, [(η³-CH₂CMeCH₂)Pd(tmps)]Cl, [(η³-CH₂CMeCH₂) Pd(teps)]Cl, [(η³-CH₂CMeCH₂)Pd(tpps)]Cl, [(η³-CH₂CMeCH₂) Pd(tbps)]Cl, [(η³-CH₂CMeCH₂)Pd(tPhps)]Cl, and [(R ₂P(S)P(S) R₂) R=Me, (tmps); Et, (teps); ⁿPr, (tpps); ⁿBu, (tbps); Ph, (tPhps)] have been prepared from the addition of tetraalkyl (phenyl)diphosphine disulfide to [(η³- CH₂CMeCH₂)Pd(μ-Cl)]₂. All the complexes have been characterized by elemental analysis, Fourier-transform infrared (FT-IR), nuclear magnetic resonance (¹H-NMR and ³¹P-{ ¹H}-NMR) spectroscopy, and fast atom bombardment (FAB) mass spectrometry. The spectroscopic studies suggest that ligands are cis-chelate bidentate coordination, forming five-membered Pd-S=P-P=S palladacycles, with the η³-allyl group completing the coordination sphere. Copyright Taylor &Francis Group, LLC.

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Synthesis and Characterization of η3-Allyl
Palladium(II) Complexes with Tetraalkyldiphosphine
Disulfides, R2P(S)P(S)R2 (R=Me, Et, nPr, nBu, Ph)
Elif Subasi a & Ozan Sanli Senturk b
a Department of Chemistry, Faculty of Science , Dokuz Eylul University , İzmir, Turkey
b Department of Chemistry, Faculty of Science and Literature , İstanbul Technical
University , Maslak, İstanbul, Turkey
Published online: 11 Aug 2011.
To cite this article: Elif Subasi & Ozan Sanli Senturk (2011) Synthesis and Characterization of η3-Allyl Palladium(II)
Complexes with Tetraalkyldiphosphine Disulfides, R2P(S)P(S)R2 (R=Me, Et, nPr, nBu, Ph), Synthesis and Reactivity in
Inorganic, Metal-Organic, and Nano-Metal Chemistry, 41:7, 834-838, DOI: 10.1080/15533174.2011.591311
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Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry, 41:834–838, 2011
Copyright ꢀ Taylor & Francis Group, LLC
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ISSN: 1553-3174 print / 1553-3182 online
DOI: 10.1080/15533174.2011.591311
Synthesis and Characterization of ␩3-Allyl Palladium(II)
Complexes with Tetraalkyldiphosphine Disulfides,
R2P(S)P(S)R2 (R=Me, Et, nPr, nBu, Ph)
Elif Subasi1 and Ozan Sanli Senturk2
1
˙
Department of Chemistry, Faculty of Science, Dokuz Eylul University, Izmir, Turkey
2
˙
Department of Chemistry, Faculty of Science and Literature, Istanbul Technical University, Maslak,
˙
Istanbul, Turkey
the preparation of the first tetraalkyldiphosphine disulfide com-
plexes in 1965 such compounds have continued[7–12] to attract
attention, in part because of the different possible coordina-
tion geometries which the ligand may adopt. In the solid state,
tetraalkyldiphosphine disulfides have the centrosymmetric trans
structure shown in Figure 1.[13] In most cases the ligand is pre-
sumed to adopt the expected cis-chelate conformation in Figure
2. It is possible for the ligand to adopt a monodentate coor-
dination such as in [Au(PPh3)(Et4P2S2)][PF6], where a single
sulfur atom coordinates to the gold center.[14] In certain reac-
tions fragmentation of the dialkyldiphosphine disulfide has been
observed. This certainly occurs when a number of square-planar
platinum complexes react with Et4P2S2.[15] The two complexes
PdX2.tmps where X=Cl or Br were assigned a structure involv-
ing a five-membered ring as in Figure 3.[16]
New allyl-palladium tetraalkyl(phenyl)diphosphine disulfide
complexes, [(η3-CH2CMeCH2)Pd(tmps)]Cl, [(η3-CH2CMeCH2)
Pd(teps)]Cl, [(η3-CH2CMeCH2)Pd(tpps)]Cl, [(η3-CH2CMeCH2)
Pd(tbps)]Cl, [(η3-CH2CMeCH2)Pd(tPhps)]Cl, and [(R2P(S)P(S)
R2) R=Me, (tmps); Et, (teps); nPr, (tpps); nBu, (tbps); Ph,
(tPhps)] have been prepared from the addition of tetraalkyl
(phenyl)diphosphine disulfide to [(η3-CH2CMeCH2)Pd(µ-Cl)]2.
All the complexes have been characterized by elemental analy-
sis, Fourier-transform infrared (FT-IR), nuclear magnetic reso-
1
nance (1H-NMR and 31P-{ H}-NMR) spectroscopy, and fast atom
bombardment (FAB) mass spectrometry. The spectroscopic studies
suggest that ligands are cis-chelate bidentate coordination, forming
five-membered Pd-S=P-P=S palladacycles, with the η3-allyl group
completing the coordination sphere.
Keywords allyl complexes, diphosphinedisulfide, palladium com-
Since studies of the reactions of η3-allylic palladium(II)
complexes containing chelating ligands with unsaturated
hydrocarbons suggest that such complexes may be useful
for a variety of organic synthesis and as model systems
for catalytic reactions,[17] we considered it worthwhile to
synthesize some η3-allyl complexes of palladium(II) with
tetraalkyldiphosphine disulfide, R2P(S)P(S)R2 (R=Me, Et,
plexes, synthesis
INTRODUCTION
The reaction of bridged [(η3-allyl)Pd(µ-X)]2 complexes
with the anion of a bidentate chelating agent may result in
monomeric products, as in the case of symmetrical and un-
symmetrical dithiocarbamate,[1] xanthate,[2] and acetylaceto-
nate[3] complexes. Halide exchange reactions can also result
in the formation of the monomeric ketoamine complexes,[4]
amino acid derivatives such as [(η3-allyl)Pd(AA)] (AA =
glycinato)[5] and bidentate phosphine sulfide complex, [(η3-
allyl)Pd(Ph2P(S)CHP(S)Ph2)], have also been reported.[6] Since
n
nPr, Bu, Ph) ligands as potentially bidentate chelating agents.
In this article, new allyl-palladium tetraalkyldiphosphine
disulfide complexes, [(η3-CH2CMeCH2)Pd(tmps)]Cl, [(η3-
CH2CMeCH2)Pd(teps)]Cl,
[(η3-CH2CMeCH2)Pd(tpps)]Cl,
[(η3-CH2CMeCH2)Pd(tbps)]Cl, [(η3-CH2CMeCH2)Pd(tPhps)]
Cl, and [(R2P(S)P(S)R2), R=Me, (tmps); Et, (teps); nPr, (tpps);
nBu, (tbps); Ph, (tPhps)] have been prepared from the addition
of tetraalkyldiphosphine disulfide to [(η3-CH2CMeCH2)Pd(µ-
Cl)]2. All the complexes have been characterized by elemental
analysis, Fourier-transform infrared (FT-IR), nuclear mag-
Received 22 November 2010; accepted 17 February 2011.
The authors thank the Research Foundation of Ege and Dokuz
Eylul University for funds. They are grateful to the technical staff of
TUBITAK (Technical and Scientific Research Council of Turkey) and
Ege University for obtaining elemental analyses and mass and NMR
spectra.
1
netic resonance (1H-NMR and 31P{ H}-NMR) spectroscopy,
and fast atom bombardment (FAB) mass spectrometry. The
spectroscopic studies suggest that ligands are cis-chelate
bidentate coordination, forming five-membered Pd-S=P-P=S
palladacycles, the η3-allyl group completing the coordination
sphere.
Address correspondence to Elif Subasi, Department of Chemistry,
˙
Faculty of Science, Dokuz Eylul University TR-35160, Izmir, Turkey.
E-mail: elif.subasi@deu.edu.tr
834

ALLYL PALLADIUM(II) COMPLEXES
835
FIG. 1. Centrosymmetric trans structure of tmps.
FIG. 3. The structure of PdX2.tmps.
n
n
phine disulfides R2P(S)P(S)R2 (R=Me, Et, Pr, Bu, Ph) were
prepared by literature methods.[20]
Synthesis of Allyl Palladium Complexes
Allyl palladium complexes were isolated by reaction of
the allylpalladium chloride complex, [(η3-CH2CMeCH2)Pd(µ-
Cl)]2 with R2P(S)P(S)R2 (R=Me, Et, nPr, nBu, Ph) and obtained
in moderate yields (60–72%) by similar methods of which the
following is typical:
[(η3-CH2CMeCH2)Pd(tmps)]Cl, was prepared by reflux-
ing Me2P(S)P(S)Me2 (0.0930 g, 0,5 mmol) and [(η3-
CH2CMeCH2)Pd(µ-Cl)]2 (0.0985 g, 0.25 mmol) together in
CH2Cl2 (10 mL) for 4 h under inert atmosphere. The solvent
was evaporated under the vacuum resulting in a dark red solid
that was extracted into tetrahydrofuran (THF, 10 mL). Addition
of petroleum ether (50 mL) resulted in precipitation of a red
solid [(η3-CH2CMeCH2)Pd(tmps)]Cl, which was washed with
petroleum ether and dried under vacuum (62% yield).
FIG. 2. Cis-chelate conformation of tmps.
EXPERIMENTAL
Materials and Measurements
Solvents were dried and degassed using standard tech-
niques.[18] Elemental analyses were performed on a Carlo Erba
Strummentaione model 1106. FT-IR spectra were measured as
KBr discs using a Perkin Elmer 1600 Fourier transform spec-
RESULTS AND DISCUSSION
1
trophotometer. H-NMR and 31P[1H]-NMR spectra in CDCl3
The synthesized series of new allyl palladium complexes
solution were recorded using a Bruker Fx 400 FT spectrometer of [(η3-CH2CMeCH2)Pd(tmps)]Cl, [(η3-CH2CMeCH2)Pd
and chemical shifts are referenced to tetramethylsilane (TMS). (teps)]Cl, [(η3-CH2CMeCH2)Pd(tpps)]Cl, [(η3-CH2CMeCH2)
All chemical shifts (δ) are quoted in parts per million (ppm) and Pd(tbps)]Cl, and [(η3-CH2CMeCH2)Pd(tPhps)]Cl, [(R2P(S)
coupling constants (J) in Hz. Positive-ion FAB mass spectra P(S)R2) R=Me, (tmps); Et, (teps); nPr, (tpps); nBu, (tbps); Ph,
were recorded on a JEOL SX102 mass spectrometer operated at (tPhps)] are presented in Scheme 1.
an accelerating voltage of 10 kV. Samples were desorbed from
a nitrobenzyl alcohol matrix using 3-keV xenon atoms.
Complexes are readily prepared in good yield from the re-
n
n
action of R2P(S)P(S)R2 (R=Me, Et, Pr, Bu, Ph) with [(η3-
Palladium complex [(η3-CH2CMeCH2)Pd(µ-Cl)]2 was pre- CH2CMeCH2)Pd(µ-Cl)]2. Characterization of complexes was
pared according to published methods[19] and tetraalkyldiphos- generally straightforward. All showed absorptions in the IR
SCH. 1. Preparation of [(η3-CH2CMeCH2)Pd(tmps)]Cl, [(η3-CH2CMeCH2)Pd(teps)]Cl, [(η3-CH2CMeCH2)Pd(tpps)]Cl, [(η3-CH2CMeCH2)Pd(tbps)]Cl, [(η3-
CH2CMeCH2)Pd(tPhps)]Cl, and [(R2P(S)P(S)R2), R=Me, (tmps); Et, (teps); nPr, (tpps); nBu, (tbps); Ph, (tPhps)].

836
E. SUBASI AND O. S. SENTURK
TABLE 1
Elemental analysis results and physical properties for the complexes
Found (calcd.) (%)
Complex
Yield (%)
Color
C
H
S
[(η3-CH2CMeCH2)Pd(tmps)]Cl
[(η3-CH2CMeCH2)Pd(teps)]Cl
[(η3-CH2CMeCH2)Pd(tpps)]Cl
[(η3-CH2CMeCH2)Pd(tbps)]Cl
[(η3-CH2CMeCH2)Pd(tPhps)]Cl
62
66
70
72
60
Red
Red
Red/brown
Red
25.75(25.07)
32.46(32.81)
48.23(48.80)
43.73(43.56)
53.56 (53.25)
4.86(4.96)
6.51(6.15)
7.17(7.07)
7.71(7.82)
4.46(4.28)
16.38(16.71)
14.97(14.58)
12.41(12.93)
11.26(11.62)
10.88(10.14)
Dark red
TABLE 2
Characteristic FTIR bands (cm−1) of the complexes
Complex
ν(η-allyl)
ν(P=S)
571 vs
551 vs
587 s
592 s
ν(P-P)
tmpsa
—
—
—
—
—
—
—
—
—
tepsa
tppsa
tbpsa
tPhpsa
—
639 vs
[(η3-CH2CMeCH2)Pd(tmps)]Cl
[(η3-CH2CMeCH2)Pd(teps)]Cl
[(η3-CH2CMeCH2)Pd(tpps)]Cl
[(η3-CH2CMeCH2)Pd(tbps)]Cl
[(η3-CH2CMeCH2)Pd(tPhps)]Cl
1460 m, 1383 s, 1352 m
1458 m, 1380 s, 1350 m
1460 m, 1380 s, 1352 m
1460 m, 1383 s, 1352 m
1462 m, 1382 s, 1349 m
582 s, 544 s
575 s, 535 s
592 s, 563 s
590 s, 565 s
601 s, 586 s
465 w
475 w
470 w
467 w
495 w
aTaken from reference [22].
spectra associated with the tetraalkyldiphosphine disulfide and out thermal decomposition. They have been characterized by
1
1
1
allyl groups, while in the H and 31P[1H]-NMR spectra indi- FT-IR, H-NMR, 31P{ H}-NMR spectroscopy and FAB mass
vidual protons were generally clearly resolved. Positive-ion fast spectrometry with data summarized in Tables 2–4.
atom bombardment (FAB) mass spectra were generally quite
Assignments are made by reference to literature data on re-
distinctive. The analytical data for complexes are listed in Table lated complexes. Since the allyl group is η3-bonded to the metal,
1. All can be stored for long periods at room temperature with- the C=C stretching band characteristic of the η1-bonded allyl
TABLE 3
1
1H and 31P{ H}-NMR data for the complexes in DMSO-d6 solutiona
Complex
Mecentral
Hanti
Hsyn
P
tmpsb
—
—
—
—
—
—
—
—
—
—
—
—
34.7 s
52.5 s
46.6 s
47.9 s
37.9 s
—
58.7 s
72.6 s
66.8 s
68.3 s
62.5 s
tepsb
tppsb
tbpsb
tPhpsb
—
—
—
[(η3-CH2CMeCH2)Pd(Cl)]2
[(η3-CH2CMeCH2)Pd(tmps)]Cl
[(η3-CH2CMeCH2)Pd(teps)]Cl
[(η3-CH2CMeCH2)Pd(tpps)]Cl
[(η3-CH2CMeCH2)Pd(tbps)]Cl
[(η3-CH2CMeCH2)Pd(tPhps)]Cl
2.12 s, 3H
2.27 s, 3H
2.27 s, 3H
2.26 s, 3H
2.25 s, 3H
2.29 s, 3H
2.86 s, 2H
2.93 s, 2H
2.92 s, 2H
2.95 s, 2H
2.93 s, 2H
2.96 s, 2H
3.84 s, 2H
3.82 s, 2H
3.80 s, 2H
3.84 s, 2H
3.82 s, 2H
3.86 s, 2H
aδ in ppm.
bTaken from reference [25].

ALLYL PALLADIUM(II) COMPLEXES
837
TABLE 4
Mass spectroscopy data for the complexes
Complex
MW
Relative intensities of the ions m/za
383 (34), [(η3-CH2CMeCH2)Pd(tmps)]Cl; 292 (21),
[(η3-CH2CMeCH2)Pd(tmps)]Cl
383
439
495
551
631
[Pd(tmps)]+2; 200 (11) [Pd(Me2P(S))]+2
404 (13), [(η3-CH2CMeCH2)Pd(teps)Et2)]+; 349 (3),
[Pd(teps)]+2; 228 (4) [Pd(Et2P(S))]+2
460 (12), [(η3-CH2CMeCH2)Pd(tpps)]+; 404 (8)
[Pd(tpps)]+2; 255 (14) [Pd(nPr 2P(S))]+2
551 (7), [(η3-CH2CMeCH2)Pd(tbps)]Cl; 461 (12),
[Pd(tbps)]+2; 284 (9), [Pd(nBu2P(S))] +2
596 (23), [(η3-CH2CMeCH2)Pd(tPhps)]+; 541 (5)
[Pd(tPhps)]+2; 324 (7), [Pd(Ph 2P(S))] +2
.
[(η3-CH2CMeCH2)Pd(teps)]Cl
[(η3-CH2CMeCH2)Pd(tpps)]Cl
[(η3-CH2CMeCH2)Pd(tbps)]Cl
[(η3-CH2CMeCH2)Pd(tPhps)]Cl
.
.
.
.
aRelative intensities are given in parentheses and assignments in square brackets. For all assignments, the most abundant isotope of Pd has
been selected (106Pd. 27.5% abundant).
group does not appear (1580–1600 cm−1). Instead, three bands
of medium or strong intensity are observed between 1462–1349
also useful for characterization. While most showed molecular
ions, these were normally weak. All of the complexes show
molecular ion peaks and have quite distinctive fragmentation
patterns.
cm−1 [21] η3-Allyl group stretching frequencies for the com-
.
plexes are in good accord with the literature assignment.[22]
The FT-IR spectra data for the complexes show a decrease
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1
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