Tellurated Schiff bases formed from {2-[(4-methoxyphenyl)telluro]ethyl} amine and bis(2-aminoethyl) telluride with o-hydroxyacetophenone: Synthesis and complexation reactions with HgII, PdII and RuII - Crystal structures of the ligands, [Ru(p-cymene)Cl{A}]Cl·H2 O and [RuCl{L2}] (see abstract)

Article abstract of DOI:10.1002/ejic.200300433

{2-[(4-Methoxyphenyl)telluro]ethyl)amine and bis(2-aminoethyl) telluride on treatment with o-hydroxyacetophenone gave the Schiff bases 4-MeOC ₆H₄TeCH₂CH₂N= C(CH ₃)C₆H₄-2-OH (L¹) and 2-HOC ₆H₄(CH₃)C= NCH₂CH ₂TeCH₂CH₂N=C(CH₃)C₆H ₄-2-OH (L³), respectively. The reduction of L¹ and L³ with NaBH₄ resulted in 4-MeOC₆H ₄TeCH₂CH₂NHCH(CH₃)C ₆H₄-2-OH (L²) and 2-HOC₆H ₄(CH₃)CHNHCH₂CH₂TeCH ₂CH₂NHCH(CH₃)C₆H₄-2-OH (L⁴), respectively, which have 1 or 2 chiral centers. The ¹H and ¹³C NMR spectra of L¹ to L⁴ were found to be characteristic. Treatment of L¹ with [Ru(p-cymene)CI₂]₂ resulted in [Ru(p-cymene)(4-MeOC ₆H₄TeCH₂CH₂NH₂)CI] CI·H₂O (1) whereas in the reaction of L² with [Ru(p-cymene)CI₂]₂, the p-cymene ligand is lost resulting in [RuCI(L²-H)] (4). The reactions of L₁, L³ and L⁴ with HgBr₂ resulted in complexes of the type [HgBr₂·(L)₂] while Na₂PdCI₄ reacted with L¹ to give [PdCI(L¹-H)]. The solid-state structures of L¹, L³, 1 and 4 were determined by single-crystal X-ray diffraction studies. The very swift formation of the tellurated amine from a tellurated Schiff base (L¹) by hydrolysis has been observed for the first time and has resulted in 1. The Ru-N and Ru-Te bond lengths in 1 are 2.142(3) and 2.6371 (4) A, respectively. The replacement of the p-cymene ligand with a hybrid organotellurium ligand (L²-H), resulting in 4, is also a first example of its kind. The Ru center in 4 has a square-planar geometry, with the Ru-N, Ru-Te, Ru-O and Ru-CI bond lengths being 2.041(6), 2.4983(8), 2.058(5) and 2.308(2) A, respectively. In the crystals of 4 there are secondary intermolecular Te...CI interactions and intermolecular N-H...O hydrogen bonds. This is the first example in which coordinated Te in a complex is engaged in two intermolecular secondary interactions. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

Full text of DOI:10.1002/ejic.200300433

FULL PAPER
Tellurated Schiff Bases Formed from {2-[(4-Methoxyphenyl)telluro]ethyl}amine
and Bis(2-aminoethyl) Telluride with o-Hydroxyacetophenone: Synthesis and
Complexation Reactions with HgII, PdII and RuII ؊ Crystal Structures of the
Ligands, [Ru(p-cymene)Cl{H2NCH2CH2TeC6H4-4-OCH3}]Cl·H2O and
[RuCl{4-MeOC6H4TeCH2CH2NHCH(CH3)C6H4-2-O؊}]
Raghavendra Kumar P.,[a] Ajai K. Singh,*[a] R. J. Butcher,[b] P. Sharma,[a] and
R. A. Toscano[c]
Keywords: Schiff bases / Ruthenium / Tellurium / X-ray diffraction / Synthetic methods
{2-[(4-Methoxyphenyl)telluro]ethyl}amine and bis(2-amino- determined by single-crystal X-ray diffraction studies. The
ethyl) telluride on treatment with o-hydroxyacetophenone
gave the Schiff bases 4-MeOC6H4TeCH2CH2N=
C(CH3)C6H4-2-OH and
(L1)
NCH2CH2TeCH2CH2N=C(CH3)C6H4-2-OH (L3), respect-
very swift formation of the tellurated amine from a tellurated
Schiff base (L1) by hydrolysis has been observed for the first
2-HOC6H4(CH3)C= time and has resulted in 1. The Ru−N and Ru−Te bond
˚
lengths in 1 are 2.142(3) and 2.6371 (4) A, respectively. The
ively. The reduction of L1 and L3 with NaBH4 resulted in 4- replacement of the p-cymene ligand with a hybrid organotel-
MeOC6H4TeCH2CH2NHCH(CH3)C6H4-2-OH (L2) and 2-
HOC6H4(CH3)CHNHCH2CH2TeCH2CH2NHCH(CH3)C6H4-
2-OH (L4), respectively, which have 1 or 2 chiral centers. The
lurium ligand (L2-H), resulting in 4, is also a first example of
its kind. The Ru center in 4 has a square-planar geometry,
with the Ru−N, Ru−Te, Ru−O and Ru−Cl bond lengths being
1H and 13C NMR spectra of L1 to L4 were found to be charac- 2.041(6), 2.4983(8), 2.058(5) and 2.308(2) A, respectively. In
˚
teristic. Treatment of L1 with [Ru(p-cymene)Cl2]2 resulted in
[Ru(p-cymene)(4-MeOC6H4TeCH2CH2NH2)Cl]Cl·H2O (1)
whereas in the reaction of L2 with [Ru(p-cymene)Cl2]2, the p-
the crystals of 4 there are secondary intermolecular Te···Cl
interactions and intermolecular N−H···O hydrogen bonds.
This is the first example in which coordinated Te in a com-
cymene ligand is lost resulting in [RuCl(L2-H)] (4). The reac- plex is engaged in two intermolecular secondary interac-
tions of L1, L3 and L4 with HgBr2 resulted in complexes of
the type [HgBr2·(L)2] while Na2PdCl4 reacted with L1 to give
tions.
( Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim,
[PdCl(L1-H)]. The solid-state structures of L1, L3, 1 and 4 were Germany, 2004)
Introduction
group containing compound. We have designed
NH2CH2CH2TeAr[5] and NH2CH2CH2TeCH2CH2NH2,[6]
which may be used for this purpose and it was therefore
thought worthwhile to synthesize the series L1 to L4. Their
metal complexes, in which a metalϪtellurium bond is
formed, are of interest and so the reactivity of these ligands
with species containing HgII, PdII and RuII has been stud-
ied. Tellurium being a very ‘‘soft’’ donor does not coordi-
nate with common species of the 3d transition metals. The
reaction of L1 with [Ru(p-cymene)Cl2]2 (p-cymene ϭ 1-
methyl-4-isopropylbenzene) resulted in [RuCl2(H2NCH2-
CH2TeC6H4OCH3)]Cl·H2O (1), in which the ligand seems
to have been generated by hydrolysis of the Schiff base L1.
This is the first example of very easy hydrolysis of a tellu-
rated Schiff base effected by traces of water present in or-
ganic solvents. The reaction of [Ru(p-cymene)Cl2]2 with L2
resulted in a complex [RuCl(L2-H)] (4) by loss of a p-cy-
mene ligand. This is also the first example where p-cymene
is replaced by a hybrid organotellurium ligand. L1, L2, 1
and 4 have been characterized by single-crystal X-ray dif-
Schiff bases have been studied extensively as ligands but
known tellurated Schiff bases are rare.[1] Some important
tellurated Schiff bases reported so far are 1,6-bis[2-(butyltel-
luro)phenyl]-2,5-diazahexa-1,5-diene,[2] Schiff bases derived
by treating bis(o-formylphenyl) telluride and o-(butyltelluro)-
benzaldehyde with chiral amines (R)-(ϩ)-[(1-phenylethyl)-
amine] and (1R,2S)-(Ϫ)-norephedrine, respectively,[3] and
macrocyclic Schiff bases.[4]
In all three instances the tellurated aldehydes were treated
with amines to prepare Schiff bases. If a tellurated amine is
treated with aldehydes or ketones then a wider range of
Schiff-base ligands may be designed by varying the carbonyl
[a]
Department of Chemistry, Indian Institute of Technology,
New Delhi 110016, India
E-mail: aksingh@chemistry.iitd.ac.in
[b]
Department of Chemistry, Howard University,
Washington, DC 20059, USA
[c]
Instituto de Quimica, UNAM,
Circuito Exterior, Coyoacan, D. F. 04510, Mexico
Eur. J. Inorg. Chem. 2004, 1107Ϫ1114
DOI: 10.1002/ejic.200300433
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1107

R. Kumar P., A. K. Singh, R. J. Butcher, P. Sharma, R. A. Toscano
FULL PAPER
fraction studies. The results of these investigations are re- ϪTeCH2 and ϪNCH2 are deshielded (δ ഠ 0.36 and
ported in this paper.
0.25 ppm, respectively) and the protons ortho and para to
the oxygen atom are shielded (δ ഠ 0.2 ppm). This is corrob-
orated by the 13C{1H} NMR spectrum of 2 and a red shift
(ca. 17 cmϪ1) in the ϾCϭNϪ stretching frequency. Unfor-
tunately, crystals of complexes 2, 3, 5 and 6 suitable for X-
ray diffraction could not be obtained. In the course of the
reaction of L1 with [Ru(p-cymene)Cl2]2; the ligand is first
hydrolyzed by traces of water present in the solvents re-
sulting in NH2CH2CH2TeC6H4-4-OMe, which generates
complex 1. This hydrolysis appears to be catalyzed by met-
allic species since in their absence it was not observed. This
is the first example where a tellurated Schiff base is hy-
drolyzed by traces of water present in the solvent so rapidly
and this is probably induced by the metal. Such metal-in-
duced hydrolysis has also been reported earlier for common
Schiff-base ligands.[7] The reaction of L2 with [Ru(p-cy-
mene)Cl2]2 resulted in the replacement of the p-cymene ring
with the Te,N,O ligand. So far no hyrbrid organotellurium
ligand has been able to displace this ring[1,8] and this is the
first example of such behaviour. However, the replacement
of the p-cymene ring in [Ru(p-cymene)Cl2]2 has been re-
ported earlier with some polydentate hybrid phosphanes.[9]
The reactions of L3 and L4 with [Ru(p-cymene)Cl2]2 and
[Ru(DMSO)4Cl2] gave intricate mixtures which are very dif-
ficult to separate.
Results and Discussion
All the tellurated Schiff bases and their reduction prod-
ucts L1 to L4 are stable and can be stored under ambient
conditions up to 6 months. They have good solubility in
CHCl3, CH2Cl2, CH3CN, EtOH and acetone. In MeOH the
solubility is moderate for L3 but good for the other three
ligands. In hexane all four ligands either are partially sol-
uble or insoluble. Complexes 1 and 4 are stable under ambi-
ent conditions and soluble in CHCl3, CH2Cl2, CH3CN,
EtOH, MeOH and acetone but insoluble in hexane. Com-
plex 2 and the mercury complexes of L1 and L3 are poorly
soluble in CHCl3 and CH2Cl2 and insoluble in hexane, ace-
tone, and acetonitrile. [HgBr2·(L4)2] is soluble in CHCl3,
CH2Cl2 and acetonitrile. All the mercury complexes, how-
ever, decompose in DMSO. All the ligands as well as 4 are
non-electrolytes. The molecular weights were found to be
consistent with the monomeric nature of L1 and L2. The
molar conductivity of 1 was found to be lower than that of
a 1:1 electrolyte probably due to association in the solution.
4 is a non-electrolyte but molecular weight measurement
suggests intermolecular association in solution. The IR
spectra of L1 and L3 are characteristic and show ϾCϭN
stretching vibrations at 1612 cmϪ1, which are absent in the
spectra of L2 and L4. The TeϪC(alkyl) vibrations are ob-
Molecular Structures of L1 and L3
The structures of L1 and L3 are shown in Figures 1 and
served in the IR spectra at 513 to 518 cmϪ1, whereas 2 with selected bond lengths and angles given in Table 1. In
TeϪC(aryl) vibrations appear at 292 cmϪ1. In all mercury L , TeϪC(11) [2.111(3) A] is shorter than TeϪC(10)
1
˚
3
˚
complexes the potentially polydentate ligands appear to co- [2.142(3) A]. For L , TeϪC(10A) and TeϪC(10B) are
˚
ordinate through the tellurium atom alone since the 2.143(4) and 2.148(4) A, respectively. These values are
ϪTeCH2 signal is deshielded (δ ഠ 0.4Ϫ0.5 ppm). The closer to that of TeϪC(10) in L1 and consistent with the
ν(HgϪBr) resonance appears in the IR spectra at 278 or earlier reports that TeϪC(aryl) bonds are shorter than
288 cmϪ1. In complex 2, the palladium atom appears to TeϪC(alkyl) bonds.[10] In L1 the angle C(11)ϪTe(1)ϪC(10)
be coordinated to a monoanionic tridentate L1 since both is
94.29(11)°
which
is
consistent
with
the
1108
 2004 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
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Eur. J. Inorg. Chem. 2004, 1107Ϫ1114

Tellurated Schiff Bases
FULL PAPER
Figure 1. Molecular structure of L1
Figure 2. Molecular structure of L3
C(10A)ϪTeϪC(10B) angle of 94.88(14)° in L3 as well as [2.619(8)Ϫ2.656(8) A] of RuII complexes of hybrid organot-
other related values reported in the literature.[10] The mol- ellurium ligands.[15] The bond angles at the Ru center are
ecules of both these ligands have intramolecular hydrogen normal. The bond angles at Te and the coordinating N
bonding. The azomethine bond length is nearly the same in atom are consistent with their nearly trigonal-pyramidal
˚
˚
both ligands, N(1)ϪC(7) is 1.284(3) A, with N(1B)ϪC(7B) [92.28(11)Ϫ106.82(9)°] and tetrahedral [120.0(2)°] geo-
˚
and N(1A)ϪC(7A) both being 1.287(4) A.
metries, respectively.
The molecular structure of 4 is shown in Figure 4 and
Molecular Structures of 1 and 4
selected bond lengths and angles are given in Table 1. The
˚
The molecular structure of 1 is shown in Figure 3 and RuϪN bond length is 2.041(6) A which is shorter than that
selected bond lengths and angles are given in Table 1. In of 1 but consistent with the literature reports mentioned
˚
the lattice of 1 there is one water molecule per molecule of above. The RuϪTe bond length 2.4983(8) A is significantly
˚
the complex. The RuϪN bond length is 2.142(3) A (sum of shorter than that of 1 and also shorter than the sum of
˚
˚
covalent radii ca. 1.95 A) and consistent with literature covalent radii of 2.62 A. The RuϪO bond length is 2.058(5)
˚
˚ ˚
reports
of
2.056(6)
A
in
[Ru(bipy)3][PF6]2,[11] A (sum of covalent radii ca. 1.91 A) and agrees with the
2.042(5)Ϫ2.154(6) A in RuII complexes of 2-(arylazo)pyrid- values of 2.034(5)Ϫ2.232(5) A reported for complexes of
˚
˚
ines,[12] 1.990(3)Ϫ2.087(5) A for Ru complexes of tetra- RuII with a variety of ligands.[16] The RuϪCl bond length
II
˚
dentate ligands based on 2,6-bis(pyrazol-1-yl)pyridine,[13] of 2.308(2) A (sum of covalent radii ca. 2.24 A) is somewhat
˚
˚
˚
˚
2.060(5) and 2.079(4) A for [Ru(p-cymene)Cl{2,3-bis(2- shorter than the reported range of 2.404(3)Ϫ2.434(1) A for
[14]
pyridyl)pyrazine}]BF4
and 2.077(3)Ϫ2.113(3) for RuII complexes of the [Ru(p-cymene)Cl2] moiety with hybrid or-
complexes of oxazoline-based ligands. The RuϪTe bond ganotellurium ligands.[15] There are two interesting features
˚
length is 2.6371(4) A which is consistent with earlier reports of the structure of 4. The first is the intermolecular second-
Eur. J. Inorg. Chem. 2004, 1107Ϫ1114
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1109

R. Kumar P., A. K. Singh, R. J. Butcher, P. Sharma, R. A. Toscano
FULL PAPER
Figure 3. Molecular structure of [Ru(p-cymene)Cl(H2NCH2CH2TeC6H4OCH3)]Cl·H2O (1)
Figure 4. Molecular structure of 4
ary interactions between each Te and two Cl atoms of center distorted pseudo-octahedral. The second feature of
neighboring
molecules
[Te··Cl
distances
of interest is the intermolecular NϪH···O hydrogen bond. The
˚
3.322(2)Ϫ3.805(2) A are less than the sum of van der Waals bond angles at Ru (Table 1) suggest that the N, O, Te and Cl
radii of 4.0 A], which makes the geometry around the Te centers are arranged around it in an almost square-planar
˚
1110
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Tellurated Schiff Bases
FULL PAPER
˚
geometry. The Te···Cl secondary interaction observed in 4
has not been reported so far for coordinated Te in any com-
plex of Te ligands. The present one is the first example of
its kind.
Table 1. Selected bond lengths [A] and angles[°]; symmetry trans-
formation used to generate equivalent atoms: #1: Ϫ x ϩ 1,Ϫy ϩ
1,Ϫz ϩ 1
L1
Te(1)ϪC(11)
Te(1)ϪC(10)
N(1)ϪC(7)
N(1)ϪC(9)
C(9)ϪC(10)
O(1)ϪC(1)
O(1)ϪH(1)
H(1)···N(1)
O(1)···N(1)
2.111(3)
2.142(3)
1.284(3)
1.470(3)
1.506(4)
1.330(3)
0.91(3)
C(11)ϪTe(1)ϪC(10)
C(7)ϪN(1)ϪC(9)
N(1)ϪC(7)ϪC(8)
N(1)ϪC(9)ϪC(10)
N(1)ϪC(7)ϪC(2)
C(16)ϪC(11)ϪTe(1)
C(12)ϪC(11)ϪTe(1)
O(1)ϪH(1)···N(1)
94.29(11)
122.6(2)
122.6(3)
108.2(2)
117.6(3)
120.2(2)
122.1(2)
155(3)
Conclusion
Tellurated Schiff bases have been synthesized from tellu-
rated amines and characterized structurally. This route has
been rarely used, however. The reactions of 4-MeOC6H4-
TeCH2CH2NϭC(CH3)C6H4-2-OH (L1) with [Ru(p-cy-
mene)Cl2]2 first results in the hydrolysis of L1 which appears
to be metal-promoted. Thereafter, the tellurated amine, (4-
MeOC6H4TeCH2CH2NH2) forms complexes with the RuII
moiety. The reaction of 4-MeOC6H4TeCH2CH2-
NHCH(CH3)C6H4-2-OH (L2) with [Ru(p-cymene)Cl2]2 re-
sulted in loss of a p-cymene ring. So far, in the reaction
of [Ru(p-cymene)Cl2]2 with Te ligands, this has never been
reported and the present example is the first of its kind. The
Te···Cl secondary interaction observed in 4 has not been
reported so far for coordinated Te in any complex of Te-
based ligands and the present one is the first example.
1.64(3)
2.496(3)
L3
TeϪC(10A)
TeϪC(10B)
2.143(4)
2.148(4)
1.466(4)
1.287(4)
1.287(4)
1.468(5)
1.347(4)
1.337(4)
0.72(4)
C(10A)ϪTeϪC(10B)
C(7A)ϪN(1A)ϪC(9A)
C(7B)ϪN(1B)ϪC(9B)
N(1A)ϪC(7A)ϪC(1A)
N(1A)ϪC(7A)ϪC(8A)
N(1B)ϪC(7B)ϪC(1B)
N(1B)ϪC(7B)ϪC(8B)
N(1B)ϪC(9B)ϪC(10B)
94.88(14)
120.6(3)
121.9(3)
116.5(3)
124.4(3)
117.2(3)
123.8(3)
109.1(3)
N(1B)ϪC(9B)
N(1B)ϪC(7B)
N(1A)ϪC(7A)
N(1A)ϪC(9A)
O(1B)ϪC(2B)
O(1A)ϪC(2A)
O(1A)ϪH(1A)
O(1B)ϪH(1B)
C(9A)ϪC(10A)
C(9B)ϪC(10B)
H(1A)···N(1A)
H(1B)···N(1B)
O(1A)···N(1A)
O(1B)···N(1B)
N(1A)ϪC(9A)ϪC(10A) 110.5(3)
0.91(5)
C(9B)ϪC(10B)ϪTe
C(9A)ϪC(10A)ϪTe
O(1A)ϪH(1A)···N(1A)
O(1B)ϪH(1B)···N(1B)
113.0(2)
115.5(2)
144(5)
1.512(5)
1.524(5)
1.89(5)
1.68(5)
2.510(4)
2.516(4)
152(4)
Experimental Section
1
General: C and H analyses were carried out with a PerkinϪElmer
Ru (1)ϪN(1)
Ru(1)ϪTe(1)
Te(1)ϪC(3)
Te(1)ϪC(2)
N(1)ϪC(1)
2.142(3)
2.6371(4) Cl(1)ϪRu(1)ϪTe(1)
2.110(3)
2.149(4)
1.481(5)
N(1)ϪRu(1)ϪTe(1)
82.48(9)
82.42(2)
elemental analyzer 240 C. Tellurium contents were estimated by
1
atomic absorption spectroscopy. The H and 13C{1H} NMR spec-
N(1)ϪRu(1)ϪCl(1)
C(2)ϪTe(1)ϪC(3)
C(3)ϪTe(1)ϪRu(1)
C(2)ϪTe(1)ϪRu(1)
C(1)ϪN(1)ϪRu(1)
85.33(10)
97.40(15)
106.82(9)
92.28(11)
120.0(2)
tra were recorded with a Bruker Spectrospin DPX-300 NMR spec-
trometer operating at 300.13 and 75.47 MHz, respectively. IR spec-
tra in the range of 4000Ϫ250 cmϪ1 were recorded with a Nicolet
´
Protege 460 FT-IR spectrometer as KBr or CsI pellets. The conduc-
tivity measurements were carried out in acetonitrile (concentration
ca. 1 m) using an ORION conductivity meter model 162. The
molecular masses (concentration ca. 5 m) in chloroform were de-
termined with a Knauer vapor pressure osmometer model A0280.
The melting points determined in open capillary are reported
as such. {2-[(4-Methoxyphenyl)telluro]ethyl}amine[5] and bis(2-
aminoethyl) telluride[6] were prepared by the reported methods.
4
Ru(1)ϪN(1)
Ru(1)ϪO(1)
Ru(1)ϪCl(1)
Ru(1)ϪTe(1)
Te(1)ϪC(11)
Te(1)ϪC(10)
Te(1)···Cl(2)#1
Te(1)···Cl(1)#1
O(1)ϪC(1)
O(2)ϪC(17)
O(2)ϪC(14)
N(1)ϪC(9)
2.041(6)
2.058(5)
2.308(2)
Ru(2)ϪN(2)
Ru(2)ϪO(3)
Ru(2)ϪCl(2)
2.048(6)
2.041(5)
2.3116(19)
2.5030(7)
2.109(7)
2.117(7)
3.322(2)
1.328(8)
1.351(9)
1.411(9)
1.501(8)
1.513(9)
2.4983(8) Ru(2)ϪTe(2)
2.113(8)
2.132(8)
3.416(2)
3.805(2)
1.323(8)
1.231(12) O(4)ϪC(34)
1.530(14) N(2)ϪC(26)
1.501(9)
1.508(9)
89.5(2)
175.66(18)
91.66(14)
90.18(18)
174.59(14)
89.03(6)
97.0(3)
Te(2)ϪC(28)
Te(2)ϪC(27)
Te(2)···Cl(1)#1
O(3)ϪC(18)
O(4)ϪC(31)
X-ray Diffraction Analyses: X-ray diffraction data for L3, 1 and 4
were collected with a Bruker Smart APEX CCD diffractometer,
˚
using graphite-monochromated Mo-Kα radiation (λ ϭ 0.71073 A)
N(2)ϪC(24)
at 293(2) K. An analytical face-indexed absorption correction was
applied. The structures where solved by direct methods. Refinement
was carried out using full-matrix least-squares analyses with aniso-
tropic thermal parameters for all non-hydrogen atoms. Hydrogen
atoms were placed in calculated positions and refined using a riding
model with fixed isotropic thermal parameters. Calculations were
carried out with SMART software for data collection and data
reduction and SHELXTL for solution and refinement.[17] A sum-
mary of relevant crystallographic results appears in Table 2. For
L1, the data were collected with a Bruker SMART 1K CCD dif-
N(1)ϪC(7)
N(1)ϪRu(1)ϪO(1)
N(1)ϪRu(1)ϪCl(1)
O(1)ϪRu(1)ϪCl(1)
N(1)ϪRu(1)ϪTe(1)
O(1)ϪRu(1)ϪTe(1)
Cl(1)ϪRu(1)ϪTe(1)
C(11)ϪTe(1)ϪC(10)
C(11)ϪTe(1)ϪRu(1)
C(10)ϪTe(1)ϪRu(1)
C(11)ϪTe(1)ϪCl(1)#1
C(10)ϪTe(1)ϪCl(1)#1
Ru(1)ϪTe(1)ϪCl(1)#
Cl(2)#1ϪTe(1)ϪCl(1)#1
C(1)ϪO(1)ϪRu(1)
C(17)ϪO(2)ϪC(14)
C(9)ϪN(1)ϪC(7)
C(9)ϪN(1)ϪRu(1)
C(7)ϪN(1)ϪRu(1)
O(3)ϪRu(2)ϪN(2)
N(2)ϪRu(2)ϪCl(2)
O(3)ϪRu(2)ϪCl(2)
N(2)ϪRu(2)ϪTe(2)
O(3)ϪRu(2)ϪTe(2)
Cl(2)ϪRu(2)ϪTe(2)
C(28)ϪTe(2)ϪC(27)
C(28)ϪTe(2)ϪRu(2)
C(27)ϪTe(2)ϪRu(2)
C(28)ϪTe(2)ϪCl(1)#1
C(27)ϪTe(2)ϪCl(1)#1
Ru(2)ϪTe(2)ϪCl(1)#1
C(18)ϪO(3)ϪRu(2)
C (31)ϪO(4)ϪC(34)
C(26)ϪN(2)ϪC(24)
C(26)ϪN(2)ϪRu(2)
C(24)ϪN(2)ϪRu(2)
92.1(2)
178.89(18)
88.99(14)
88.84(17)
178.94(14)
90.05(6)
93.4(3)
96.07(19)
89.46(18)
171.4(2)
78.1(2)
85.18(4)
125.7(4)
117.4(7)
110.0(5)
117.6(4)
111.9(4)
97.4(2)
87.3(2)
80.3(2)
131.5(2)
141.28(4)
97.06(5)
126.8(5)
103.9(13)
111.3(6)
117.6(5)
110.4(4)
˚
fractometer using X-rays of wavelength 0.71073 A (Mo-Kα source).
A semiempirical absorption correction was applied.[18] Cell refine-
ment was done with the SMART and SAINT programs.[19] The
structure was solved in a similar manner to those of L3, 1 and 2
using SHELXTL.[20] CCDC-214420 (1), -214421 (L1), -214422 (4)
and -214423 (L3) contain the supplementary crystallographic data
for this paper. These data can be obtained free of charge at
Eur. J. Inorg. Chem. 2004, 1107Ϫ1114
www.eurjic.org
 2004 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
1111

R. Kumar P., A. K. Singh, R. J. Butcher, P. Sharma, R. A. Toscano
FULL PAPER
Table 2. Crystal data and structural refinements for L1, L3, 1 and 4
L1
L3
1
4
Empirical formula
Formula mass
Color
C17H19NO2Te
396.93
yellow
C20H24N2O2Te
452.01
yellow
C19H29Cl2NO2RuTe
603.00
orange
C17H20ClNO2RuTe
534.46
orange
Crystal size [mm]
Crystal system
Space group
0.262 ϫ 0.076 ϫ 0.066
monoclinic
P21/c
a ϭ 16.399(1)
b ϭ 7.5318(4)
c ϭ 13.368(1)
β ϭ 101.909(1)
1615.6(2)
0.02 ϫ 0.02 ϫ 0.66
monoclinic
P21/c
a ϭ 14.6456(12)
b ϭ 18.8812(15)
c ϭ 6.9923(5)
β ϭ 98.902(2)
1910.3(3)
0.126 ϫ 0.126 ϫ 0.114
monoclinic
P21/c
a ϭ 10.2639(4)
b ϭ 19.459(1)
c ϭ 10.964(1)
β ϭ 95.202(2)
2180.9(2)
0.218 ϫ 0.214 ϫ 0.194
monoclinic
P21/n
a ϭ 14.725(1)
b ϭ 13.276(1)
c ϭ 20.562(2)
β ϭ 99.052(2)
3969.6(6)
˚
Unit cell dimensions [A, °]
3
˚
Volume [A ]
Z
4
4
4
8
Density (calcd.) [Mg·mϪ3
Absorption coefficient [mmϪ1
F(000)
]
1.632
1.845
784
1.572
1.572
904
1.837
2.288
1184
1.789
2.372
2064
]
θ range [°]
Index ranges
2.54Ϫ25.01
Ϫ19 Յ h Յ 19
Ϫ8 Յ k Յ 8
Ϫ15 Յ l Յ 15
12714
2.16Ϫ24.73
Ϫ16 Յ h Յ 17
Ϫ22 Յ k Յ 21
Ϫ8 Յ l Յ 8Յ
11272
1.99Ϫ24.99
Ϫ12 Յ h Յ 12
Ϫ23 Յ k Յ 23
Ϫ13 Յ l Յ 13
17640
1.83Ϫ25.03
Ϫ17 Յ h Յ 17
Ϫ15Յ k Յ15
Ϫ24 Յ l Յ 24
32038
Reflections collected
Independent reflections
Completeness to maximum θ [%] 99.8
2832 [R(int) ϭ 0.0441]
3255 [R(int) ϭ 0.0513]
99.8
3825 [R(int) ϭ 0.0440]
99.9
7012 [R(int) ϭ 0.0570]
100.0
Max./min. transmission
Data/restraints/parameters
Goodness-of-fit on F2
Final R indices [I Ͼ 2σ(I)]
R indices (all data)
0.8970/0.7222
2832/0/195
0.959
0.928019/0.782123
3255/0/236
0.992
0.8165/0.6977
3825/0/351
1.033
0.6831/0.6116
7012/0/425
0.997
R1 ϭ 0.0283, wR2 ϭ 0.0524 R1 ϭ 0.0278, wR2 ϭ 0.0574 R1 ϭ 0.0265, wR2 ϭ 0.0408 R1 ϭ 0.0478, wR2 ϭ 0.1067
R1 ϭ 0.0415, wR2 ϭ 0.0551 R1 ϭ 0.0480, wR2 ϭ 0.0636 R1 ϭ 0.0342, wR2 ϭ 0.0423 R1 ϭ 0.0722, wR2 ϭ 0.1159
0.541/Ϫ0.243
Ϫ3
˚
˚
Largest diff. peak/hole [e·A
]
0.610/Ϫ0.387.
0.473/Ϫ0.416
1.027 (0.83 A from Ru2)/Ϫ0.572
www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge
Crystallographic Data Center, 12 Union Road, Cambridge CB2
ant precipitate was recrystallized from chloroform/hexane (1:1).
The dark-red crystals of 1 were washed immediately with dichloro-
1EZ, UK; Fax: (internat.) ϩ 44-1223/336-033; E-mail: deposit@- methane and recrystallized again to give dark-orange single crys-
ccdc.cam.ac.uk].
tals. Yield ca. 0.85 g (ca. 60%); m.p. 160 °C (dec.). ΛM ϭ 43.0
cm2·molϪ1·ohmϪ1
.
Molecular mass: calcd. 603; found 648.
Synthesis of L1: {2-[(4-Methoxyphenyl)telluro]ethyl}amine (1.39 g,
5.0 mmol) was stirred in dry ethanol (20 mL) at room temperature
for 0.5 h. o-Hydroxyacetophenone (0.68 g, 5.0 mmol), dissolved in
dry ethanol (20 mL), was added to the above solution dropwise
with stirring. The mixture was stirred at room temp. for a further
2 h. The solvent was evaporated in a rotary evaporator resulting
in a yellow precipitate. The precipitate, on recrystallization from
chloroform/hexane (1:1), afforded yellow single-crystals of L1.
C19H27Cl2NORuTe·H2O (603): calcd. C 39.01, H 4.65, N 2.39, Te
21.81; found C 38.97, H 4.83, N 2.56, Te, 21.22. 1H NMR (CDCl3,
25 °C, TMS): δ ϭ 1.22 (d, J ϭ 6.6 Hz, 3 H, CH3 of iPr), 1.315 (d,
J ϭ 6.6 Hz, 3 H, CH3 of iPr), 2.27 (s, 3 H, CH3 p to iPr), 2.69Ϫ2.74
(sept, 1 H, CH of iPr), 2.69Ϫ2.72 (t, 2 H, TeCH2), 3.53Ϫ3.56 (t, 2
H, NCH2), 3.83 (s, 3 H, OCH3), 5.13Ϫ5.96 (m, 4 H, ArH of p-
cymene), 7.045 (d, J ϭ 8.4 Hz, 2 H, ArH m to Te), 8.005 (d, J ϭ
8.7 Hz, 2 H, ArH o to Te), 8.46 (br. s, 2 H, NH2) ppm. 13C{1H}
NMR (CDCl3, 25 °C, TMS): δ ϭ 17.28 (TeCH2), 18.89 (p-cymene
CH3), 24.69 and 25.73 (CH3 of iPr of p-cymene), 30.75, 31.41 (CH
of iPr of p-cymene), 42.55 (NCH2), 55.36 (OCH3), 76.58Ϫ85.13
(ArC of p-cymene m and o to iPr), 101.51 (ArCTe), 104.75
(ArCCH3 of p-cymene), 105.88 (ArC-iPr of p-cymene),
115.15Ϫ116.34 (ArC m to Te), 138.09 (ArC o to Te), 161.69 (Ar-
COCH3) ppm. IR (KBr): nu(tilde ) ϭ 361 ν(RuϪCl), 440
Yield 1.61 g (85%); m.p. 82Ϫ83 °C. ΛM ϭ 0.9 cm2·molϪ1·ohmϪ1
C17H19NO2Te (396.9): calcd. C 51.44, H, 4.82, N 3.53, Te 32.15;
found C 51.26, H 4.81, N 3.16, Te 31.86. Molecular mass: calcd.
.
1
396.6; found 399.0. H NMR (CDCl3, TMS, 25 °C): δ ϭ 2.27 (s, 3
H, CH3), 3.13 (t, 2 H, 2-H), 3.81 (s, 3 H, OCH3), 3.92 (t, 2 H, 1-
H), 6.76Ϫ6.82 (m, 3 H, ArH m to Te and 7-H), 6.945 (d, J ϭ
8.4 Hz, 1 H, 9-H), 7.30Ϫ7.32, (m, 1 H, 8-H), 7.505 (d, J ϭ 8.1 Hz,
1 H, 6-H), 7.745 (d, J ϭ 8.4 Hz, 2 H, ArH o to Te), 16.00 (br. s, 1
H, OH) ppm. 13C{1H} NMR (CDCl3, 25 °C, TMS): δ ϭ 8.32
(CH3), 14.54 (C-2), 50.87 (C-1), 55.11 (OCH3), 99.67 (ArCTe),
115.21 (ArC m to Te), 117.11 (C-6), 118.63 (C-8), 119.10 (C-4),
127.97 (C-9), 132.40 (C-7), 141.34 (ArC o to Te), 159.90 (Ar-
COCH3), 163.53 (C-5), 171.38 (C-3) ppm.
ν(RuϪN) cmϪ1
.
Synthesis of [PdCl(L1-H)] (2): Na2[PdCl4] (0.294 g, 1 mmol) was
dissolved in water (5 mL). A solution of L1 (0.397 g, 1 mmol) pre-
pared in acetone (10 mL) was added with vigorous stirring. An
orange precipitate of 2 was immediately obtained which was filtered
and dried. The orange solid was recrystallized from chloroform/
Synthesis of [Ru(p-cymene)Cl(H2NCH2CH2TeC6H4-4-OCH3)]-
Cl·H2O (1): [RuCl2(p-cymene)]2 (0.62 g, 1 mmol) was dissolved in methanol/hexane to give crystals of 2. Yield ca. 0.37 g (ca.72%);
dichloromethane (10 mL). A solution of L1 (0.79 g, 2 mmol), pre-
pared in dichloromethane (20 mL), was added with vigorous stir-
m.p. 162 °C. C17H18ClNO2PdTe (533.8): calcd. C 37.97, H 3.37,
N 2.60, Te 23.80; found C 39.48, H 3.47, N 2.43, Te 23.65. 1H
ring. The mixture was stirred for a further 3 h. The solvent was NMR (CDCl3, 25 °C, TMS): δ ϭ 2.39 (s, 3 H, CH3), 3.49 (t, 2 H,
removed in a rotary evaporator under reduced pressure. The result- 2-H), 3.82 (s, 3 H, OCH3), 4.17 (t, 2 H, 1-H), 6.61Ϫ6.66 (m, 3 H,
1112
 2004 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
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Eur. J. Inorg. Chem. 2004, 1107Ϫ1114

Tellurated Schiff Bases
FULL PAPER
ArH m to Te and 7-H), 6.915 (d, J ϭ 8.7 Hz, 1 H, 9-H), 7.12Ϫ7.14, (d, J ϭ 8.1 Hz, 2 H, 9-H) 7.26Ϫ7.30 (t, 2 H, 7-H), 7.502 (d, J ϭ
(m, 1 H, 8-H), 7.335 (d, J ϭ 9.0 Hz, 1 H, 6-H), 8.065 (d, J ϭ
8.1 Hz, 2 H, 6-H), 15.93 (br. s, 1 H, OH) ppm. 13C{1H} NMR
9.0 Hz, 2 H, ArH o to Te) ppm. 13C{1H} NMR (CDCl3, 25 °C, (CDCl3, 25 °C, TMS): δ ϭ 3.49 (C-2), 14.73 (CH3), 51.64 (NCH2),
TMS): δ ϭ 13.38 (CH3), 19.29 (C-2), 62.76 (C-1), 55.01 (OCH3), 117.27 (C-6), 118.57 (C-8), 119.36 (C-4), 128.06 (C-9), 132.43 (C-
102 (ArCTe), 115.38 (ArC m to Te), 115.71 (C-6), 120.86 (C-8), 7), 163.32 (C-5), 171.60 (C-3) ppm.
125.01 (C-4), 127.68 (C-9), 130.86 (C-7), 138.58 (ArC o to Te),
Synthesis of [HgBr2(L3)2] (5): HgBr2 (0.360 g, 1 mmol) was dis-
159.90 (ArCOCH3), 163.53 (C-5), 171.38 (C-3) ppm. IR (KBr): ν˜ ϭ
solved in acetone (5 mL). A solution of L3 (0.904 g, 2 mmol), pre-
pared in chloroform (10 mL), was added with stirring. The mixture
was stirred for a further 1 h. A yellow solid separated out which
was filtered, washed with acetone and dried. Yield 1.01 g (80%);
m.p. 142 °C. C34H38Br2HgN2O2Te2 (1264): calcd. Te 20.25; found
Te 19.88. 1H NMR (CDCl3, 25 °C, TMS): δ ϭ 2.29 (s, 12 H, CH3),
3.49Ϫ3.53 (t, 8 H, 2-H), 4.07Ϫ4.11 (t, 8 H, 1-H), 6.75Ϫ6.80 (t, 4
H, 8-H), 6.873 (d, J ϭ 8.1 Hz, 4 H, 9-H), 7.22Ϫ7.27 (m, 4 H, 7-
H), 7.48 (d, J ϭ 6.9 Hz, 4 H, 6-H), 15.13 (br. s, OH) ppm.
306 ν(PdϪCl), 486 ν(PdϪN) cmϪ1
.
Synthesis of [HgBr2·(L1)2] (3): HgBr2 (0.720 g, 2 mmol) was dis-
solved in acetone (5 mL). A solution of L1 (1.588 g, 4 mmol), pre-
pared in chloroform (10 mL), was added with stirring. The mixture
was stirred for a further 0.5 h. A yellow solid separated out which
was filtered, washed with acetone and dried. Yield 1.66 g (ca. 85%);
m.p. 138 °C. C34H38Br2HgN2O2Te2 (1154): calcd. Te 22.8; found
1
Te 21.6. H NMR (CDCl3, 25 °C, TMS): δ ϭ 2.38 (s, 6 H, CH3),
3.56 (t, 4 H, 2-H), 3.82 (s, 6 H, OCH3), 4.04 (t, 4 H, 1-H),
6.80Ϫ6.83 (m, 3 H, ArH m to Te and 7-H), 6.925 (d, J ϭ 9.0 Hz
1 H, 9-H), 7.505 (d, J ϭ 7.8 Hz, 1 H, 6-H), 7.745 (d, J ϭ 8.7 Hz,
2 H, ArH o to Te) ppm; signal due to 8-H merged with that of
chloroform (δ ϭ 7.26 ppm).
Synthesis of L4: L3 (0.452 g, 1 mmol) and NaBH4 (0.38 g, 10 mmol)
were heated to reflux in dry ethanol (100 mL) for 24 h. The solu-
tion was cooled and the solvent was evaporated in vacuo. The li-
gand was extracted with dichloromethane and the extract dried
with sodium sulfate. The solvent was removed in vacuo affording
L4 as a highly viscous pale yellow oil. Yield 0.31 g (67%); ΛM
ϭ
Synthesis of L2: L1 (0.40 g, 1 mmol) and NaBH4 (0.38 g, 10 mmol)
were heated to reflux in dry ethanol (100 mL) for 24 h. The solu-
tion was cooled and the solvent was evaporated in vacuo. The li-
gand was extracted with dichloromethane and the extract dried
with sodium sulfate. The solvent was removed in vacuo. L2 was
obtained as highly viscous pale yellow oil. Yield 0.28 g (70%);
ΛM ϭ 0.4 cm2·molϪ1·ohmϪ1. C17H21NO2Te (399): calcd. Te 31.98;
0.90 ohmϪ1·cm2·molϪ1. C17H21NO2Te (456): calcd. Te 25.52; found
1
Te 24.93. H NMR (CDCl3, 25 °C, TMS): δ ϭ 1.361, 1.365 (2 d,
J ϭ 6.6, 9.9 Hz, 6 H, CH3), 2.54Ϫ2.75 (m, 8 H, 1-H ϩ 2-H),
3.83Ϫ3.84 (m, 2 H, CH), 6.67Ϫ6.74 (m, 4 H, 7-H ϩ 9-H), 6.86 (d,
J ϭ 7.2 Hz, 2 H, 6-H), 7.03Ϫ7.08 (m, 2 H, 8-H), 11.40 (very br. s,
OH) ppm.
1
found Te 31.31. H NMR (CDCl3, 25 °C, TMS): δ ϭ 1.38 (d, J ϭ
Synthesis of [HgBr2(L4)2] (6): HgBr2 (0.360 g, 1 mmol) was dis-
solved in acetone (5 mL). A solution of L4 (0.904 g, 2 mmol), pre-
pared in chloroform (10 mL), was added with stirring. The mixture
was stirred for a further 1 h. A yellow solid separated out which
was filtered, washed with acetone and dried. Yield 1.02 g (ca.80%);
m.p. 105 °C. C34H38Br2HgN2O2Te2 (1272): calcd. Te 20.12; found
Te 19.35. 1H NMR (CDCl3, 25 °C, TMS): δ ϭ 2.16 (s, 12 H, CH3),
2.81 (br. s, 8 H, 1-H), 3.10 (br. s, 8 H, 2-H), 3.99 (m, 2 H, CH),
6.77Ϫ6.79 (m, 4 H, 7-H ϩ 9-H), 6.99 (d, J ϭ 6 Hz, 2 H, 6-H),
7.09Ϫ7.11 (m, 2 H, 8-H) ppm.
6.6 Hz, 3 H, CH3), 1.87Ϫ1.97 (br. s, 1 H, NH), 2.83Ϫ2.98 (m, 4
H, 1-H ϩ 2-H), 3.78 (s, 3 H, OCH3), 3.83Ϫ3.88 (m, 1 H, CH),
6.71Ϫ6.79 (m, 4 H, ArH m to Te and 7-H ϩ 9-H), 6.885 (d, J ϭ
7.5 Hz, 1 H, 6-H), 7.09Ϫ7.14 (m, 1 H, 8-H), 7.655 (d, J ϭ 8.7 Hz,
2 H, ArH o to Te), 11.40 (very br. s, OH) ppm. 13C{1H} (CDCl3,
25 °C, TMS): δ ϭ 8.83 (C-1), 22.27 (CH3), 47.65 (C-1), 55.09
(OCH3), 58.19 (C-3) 99.67 (ArCTe), 115.29 116.67 (ArC m to Te),
118.95 (C-6), 120.20 (C-8), 126.50 (C-4), 127.90 (C-9), 128.26 (C-
7), 140.23Ϫ141.07 (ArC o to Te), 157.12 (ArCOCH3), 159.91 (C-
5) ppm.
Synthesis of [RuCl(L2-H)] (4): [RuCl2(p-cymene)]2 (0.62 g, 1 mmol)
was dissolved in dichloromethane (10 mL). A solution of L2
(0.80 g, 2 mmol), prepared in dichloromethane (20 mL), was added
with vigorous stirring. The mixture was stirred for a further 3 h.
The solvent was removed in a rotary evaporator under reduced
pressure. The dark orange single crystals of 4 were grown from
chloroform/hexane (1:1). Yield 0.72 g (67%); m.p. 100 °C (dec.).
Acknowledgments
R. K. P. thanks UGC (India) for a fellowship. A. K. S. thank CSIR
(India) for the research project no. 1(1849)/03/EMR-II. P. S., on
leave from Instituto de Quimica, UNAM, is thankful to DGAPA,
UNAM for financing a sabbatical stay at IITD.
Molecular mass: calcd. 535.41; found 1037. ΛM
ϭ 0.9
cm2·molϪ1·ohmϪ1. C17H20ClNO2RuTe (534.4): calcd. C 38.21, H
[1] [1a]
A. K. Singh, V. Srivastava, J. Coord. Chem. 1992, 27,
237Ϫ253. [1b] A. K. Singh, S. Sharma, Coord. Chem. Rev. 2000,
209, 49Ϫ98.
3.77, N 2.62, Te 23.88; found C 39.01, H 4.20, N 2.22, Te 23.16.
IR (KBr): ν˜ ϭ 361 ν(RuϪCl), 450 ν(RuϪN) cmϪ1
.
[2]
N. Al-Salim, T. A. Hamor, W. R. McWhinnie, J. Chem. Soc.,
Chem. Commun. 1986, 453Ϫ455.
S. C. Menon, A. Panda, H. B. Singh, R. J. Butcher, Chem.
Commun. 2000, 143Ϫ144.
S. C. Menon, H. B. Singh, R. P. Patel, R. J. Butcher, Organome-
tallics 1997, 16, 563Ϫ571.
A. K. Singh, V. Srivastava, Phosphorus, Sulfur Silicon Relat
Elem. 1990, 47, 471Ϫ475.
V. Srivastava, R. Batheja, A. K. Singh, J. Organomet. Chem.
1994, 484, 93Ϫ96.
G. L. Eichhorn, J. C. Bailar Jr., J. Am. Chem. Soc. 1953, 75,
2905Ϫ2907; I. Jardine, F. J. McQuillin, Tetrahedron Lett.
1972, 459Ϫ461.
A. K. Singh, Proc. Indian Acad. Sci. (Chem. Sci.) 2002, 114,
357Ϫ366.
Synthesis of L3: Bis(2-aminoethyl) telluride (1.13 g, 2.5 mmol) was
stirred at room temperature in dry ethanol (20 mL) for 0.5 h. 2-
Hydroxyacetophenone (0.68 g, 5 mmol), dissolved in dry ethanol
(20 mL), was added to the above solution dropwise with stirring.
The mixture was stirred at room temp. for a further 6 h, was then
kept at 0Ϫ5 °C for 24 h. L3 separated as a yellow precipitate. The
precipitate was recrystallized at 0Ϫ5 °C from chloroform/hexane
(1:1) to give yellow single crystals of L3. Yield 1.13 g (80%); m.p.
95Ϫ96 °C. ΛM ϭ 0.86 cm2·molϪ1·ohmϪ1. Molecular mass: calcd.
452; found 444.5. C20H24N2O2Te (452): calcd. C 53.14, H, 5.35, N
[3]
[4]
[5]
[6]
[7]
1
6.20, Te 28.23; found C 52.52, H 5.42, N 6.74, Te 27.66. H NMR
[8]
(CDCl3, 25 °C, TMS): δ ϭ 2.32 (s, 6 H, CH3), 3.02Ϫ3.07 (t, 4 H,
TeCH2), 3.94Ϫ3.99 (t, 4 H, 1-H), 6.75Ϫ6.80 (m, 2 H, 8-H), 6.915
Eur. J. Inorg. Chem. 2004, 1107Ϫ1114
www.eurjic.org
 2004 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
1113

R. Kumar P., A. K. Singh, R. J. Butcher, P. Sharma, R. A. Toscano
FULL PAPER
[9]
P. Braunstein, F. Naud, A. Pfaltz, S. J. Rettig, Organometallics
samy, G. S. Murthy, J. Srinivas, B. Varghese, R. J. Butcher, J.
Organomet.Chem., 2000, 605, 39Ϫ44.
2000, 19, 2676Ϫ2683.
A. K. Singh, J. Sooriyakumar, M. Kadarkaraisamy, J. E.
[16]
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Received July 5, 2003
Early View Article
Published Online February 5, 2004
1114
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