Synthesis and characterization of tri-, di-, and chlorodiorganotin(IV) derivatives of 3-benzoyl-α-methylphenylacetic acid and 3-(2-thienyl)acrylic acid

Article abstract of DOI:10.1081/SIM-120013143

Various organotin derivatives of 3-benzoyl-α-methylphenylacetic acid (HL¹) and 3-(2-thienyl)acrylic acid (HL²) of the general formulae R₃SnL, R₂SnL₂ and R₂Sn(Cl)L where R=Me, Et, n-Bu and P

Full text of DOI:10.1081/SIM-120013143

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SYNTHESIS AND CHARACTERIZATION OF TRI-, DI-,
AND CHLORODIORGANOTIN(IV) DERIVATIVES OF 3-
BENZOYL-α-METHYLPHENYLACETIC ACID AND 3-(2-
THIENYL)ACRYLIC ACID
Muhammad Tariq Masood a , Saqib Ali b , Muhammad Danish a & Muhammad Mazhar a
a Department of Chemistry , Quaid-i-Azam University , 45320 Islamabad, Pakistan
b Department of Chemistry , Quaid-i-Azam University , 45320 Islamabad, Pakistan
Published online: 15 Feb 2007.
To cite this article: Muhammad Tariq Masood , Saqib Ali , Muhammad Danish & Muhammad Mazhar (2002) SYNTHESIS AND
CHARACTERIZATION OF TRI-, DI-, AND CHLORODIORGANOTIN(IV) DERIVATIVES OF 3-BENZOYL-α-METHYLPHENYLACETIC
ACID AND 3-(2-THIENYL)ACRYLIC ACID, Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 32:1, 9-23, DOI:
10.1081/SIM-120013143
To link to this article: http://dx.doi.org/10.1081/SIM-120013143
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SYNTH. REACT. INORG. MET.-ORG. CHEM., 32(1), 9–23 (2002)
SYNTHESIS AND CHARACTERIZATION
OF TRI-, DI-, AND
CHLORODIORGANOTIN(IV)
DERIVATIVES OF 3-BENZOYL-a-
METHYLPHENYLACETIC ACID AND
3-(2-THIENYL)ACRYLIC ACID
Muhammad Tariq Masood, Saqib Ali,* Muhammad
Danish, and Muhammad Mazhar
Department of Chemistry, Quaid-i-Azam University,
45320 Islamabad, Pakistan
ABSTRACT
Various organotin derivatives of 3-benzoyl-a-methylphenyla-
cetic acid (HL1) and 3-(2-thienyl)acrylic acid (HL2) of the
generalformuale R 3SnL, R2SnL2 and R2Sn(Cl)L where
R ¼ Me, Et, n-Bu and Ph, L ¼ L1 or L2, have been synthe-
sized. These compounds were characterized by elemental
analyses, infrared, mass, 1H, 13C and 119Sn NMR spectra and
the geometry around the tin atom has been discussed.
*Corresponding author. E-mail: drsa54@yahoo.com
9
Copyright # 2002 by MarcelDekker, Inc.
www.dekker.com

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MASOOD ET AL.
INTRODUCTION
Since the last two decades173, organotin carboxylates have been se-
lected as candidates for the study of their diversified applications and in-
teresting structures. Their spectroscopic studies show that there are distinct,
phase-dependent geometries around the tin atom in non-coordinating sol-
vents as well as in the solid state477
.
In continutaion of our previous research work8715, we report here the
synthesis, infrared, mass and multinuclear (1H, 13C, 119Sn) NMR spectra of
new organotin(IV) carboxylates of 3-benzoyl-a-methylphenylacetic acid
(HL1) and 3-(2-thienyl)acrylic acid (HL2).
RESULTS AND DISCUSSION
Tri-, di- and monochloroorganotin carboxylates of the ligands HL1
and HL2 were prepared by the following general reactions (1)7(3). The
elemental analyses and some of their physical data are given in Table I.
R3SnCl þ AgL1À! R3SnL1 þ AgCl
R ¼ Með1Þ; n-Buð4Þ and Phð6Þ
ð1Þ
R2SnO þ 2LHÀ! R2SnL2 þ H2O
ð2Þ
ð3Þ
L ¼ L1; R ¼ Etð2Þ; n-Buð3Þ and Phð5Þ
L ¼ L2; R ¼ Etð7Þ; n-Buð9Þ and Phð11Þ
R2SnL22 þ R2SnCl2À! 2R2SnðClÞL2
R ¼ Etð8Þ; n-Buð10Þ and Phð12Þ
Infrared Spectroscopy
In the infrared region, the bands of interest are n(COO), n(Sn-C),
n(Sn-O) and n(Sn-Cl) as given in Table II. A marked shifting is observed in
the COO frequencies for the complexes as compared to the free acid. This
vibration is very important in the prediction of the bonding mode of the
ligand. As shown in Table II, the Dn values ½Dn ¼ nasymðCOOÞ ÀnsymðCOOފ

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TRI-, DI-, AND CHLORODIORGANOTIN(IV) DERIVATIVES
11

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12
MASOOD ET AL.
Table II. Assignments of Characteristic Infrared Vibrations (cmÀ1
)
n(COO)
Comp.
Asym.
Sym.
Dn
n(Sn-C)
n(Sn-O)
n(Sn-Cl)
HL1
HL2
AgL1
AgL2
(1)
1677 s
1688 s
1560 s
1544 s
1550 s
1560 s
1562 s
1573 s
1553 s
1565 s
1555 s
1552 s
1563 s
1566 s
1572 s
1574 s
1420 s
1419 s
1390 s
1392 s
1370 s
1365 s
1370 s
1381 s
1366 s
1382 s
1376 s
1374 s
1370 s
1370 s
1371 s
1374 s
257
269
170
152
180
195
192
192
187
183
179
178
193
196
201
200
7
7
7
7
7
7
7
7
7
7
7
7
7
7
7
7
7
546 m
592 m
548 m
602 s
598 s
602 s
608 m
594 m
608 s
592 m
606 m
590 s
417 w
438 m
436 m
417 m
480 s
447 w
488 w
448 w
488 s
448 m
482 m
444 m
(2)
(3)
(4)
(5)
(6)
(7)
7
7
357 s
(8)
(9)
(10)
(11)
(12)
7
348 m
7
353 s
are comparable to the values of the silver salts which clearly indicate the
bidentate nature of the ligands16. Thus, for triorganotin complexes a brid-
ging nature is most likely and is further supported by the crystal structure of
the trimethyldrivative of compound 123. In case of the chlorodiorganotin
derivatives, the presence of a chlorine atom increases the Lewis acidity of
tin, thus increasing tin-carbonylinteraction which propose the bridging or
chelating nature the of ligand. However, the chelating mode of interaction is
more favourable and is suggested for such compounds17. For the R2SnL2
compounds, a bidentate chelate nature of the corboxylate is suggested which
24
is further suported by the crystalstructure of the diethyltin derivative of
the ligand HL2. The bands in the range 6007500 cmÀ1 and 5007400 cmÀ1
indicate Sn-C and Sn-O bonds, respectively. In the chloro derivatives the
Sn-Clband is observed in the region 357 7348 cmÀ1. The band position of
1
the carbonylgroup between two benzene rings of the ilgand HL
affected, showing the non-involvment of this group in bonding to tin.
is un-
MultinuclearNMR
Multinuclear NMR spectra have been carried out in CDCl3. The
expected resonances were assigned on the basis of their intensity and

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TRI-, DI-, AND CHLORODIORGANOTIN(IV) DERIVATIVES
13
multiplicity pattern as well as their coupling constants. The peak integra-
tions of the spectra are in accordance with the number of protons proposed
for each fragment of the molecule. The numbering scheme for ligands is
given in Fig. 1. The aromatic carbon resonances were assigned by com-
paring experimentalchemicalshifts with those calculated by the incremental
method18a and literature values18b
.
In triorganotin carboxylates 1J[119Sn-13C], the indirect tin proton
coupling constants 2J[119Sn-1H] and 119Sn chemicalshifts (Tabels I, III 7VI)
describe a tetrahedralgeometry around the tin atom
19,20
.
For trimethyltin 3-benzoyl-a-methylphenylacete, 1J[119Sn-13C] and
2J[119Sn-1H] are 400 and 58.2 Hz, respectively. Using Lockhart’s and
Holecek’s relations21,22, the C-Sn-C bond angle calculated for this com-
pound is 111ꢀ. However, this angle is a little bit less than the C-Sn-C bond
angle obtained from the crystal structure of this compound23. This shows
that there are two distinct, phase-dependent geometries around the tin atom
in such compounds. Therefore, the average C-Sn-C angle (111ꢀ) suggests a
monomeric tetrahedralenvironment around the tin atom in non-co-
ordinating solvents. In the solid phase, however, such compounds have a
distorted trigonalbipyramidalgeometry with a polymeric structure 8,23. It is,
therefore, suggested that all of the triorganotin derivatives are monomeric in
non-coordinating solvents with tetrahedral geometry (Fig. 2(a)) and are
polymeric in the solid state (Fig. 2(b)).
Unlike triorganotin carboxylates in solution, the geometry of dior-
ganotin carboxylates cannot be defined with certainty because of dynamic
processes involving the carboxylate oxygens due to competition in their
coordination behaviour with the tin atom9. However, in the solid state the
tin atom is hexa-coordinated in such systems24 (Fig. 2(c)).
In chlorodiorganotin carboxylates, 1J[119Sn-13C] and 2J[119Sn-1H]
could only be resolved for Et2Sn(Cl)L (Tables V and VI) due to very broad
Figure 1. Structures of the ligands.

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MASOOD ET AL.

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TRI-, DI-, AND CHLORODIORGANOTIN(IV) DERIVATIVES
15
Table IV. 13C NMR Dataa,b,c of Tri- and Diorganotin Carboxylates of HL1
Compound
?
Carbon;
(1)
R ¼ Me
(2)
R ¼ Et
(3)
R ¼ n-Bu
(4)
R ¼ n-Bu
(5)
R ¼ Ph
(6)
R ¼ Ph
1
2
3
4
5
6
7
8
132.4
130.0
143.0
128.6
128.4
132.4
196.6
138.0
129.2
128.3
131.6
29.7
179.0
19.4
À2.3
1J[400]
7
132.4
130.0
141.0
129.0
128.5
132.4
196.5
137.8
129.1
128.3
131.5
29.7
132.3
130.0
142.4
128.5
128.2
132.3
196.4
137.9
129.3
128.2
131.6
26.8
132.3
130.0
142.4
128.5
128.2
131.6
196.6
137.6
129.3
128.3
131.8
26.9
132.6
131.7
140.1
131.6
128.6
132.6
196.0
137.4
129.3
128.3
128.6
29.7
135.3
131.5
141.5
128.9
128.0
132.2
196.3
136.6
129.3
128.3
129.2
29.6
9/13
10/12
11
14
15
16
a
184.3
18.8
17.5
179.1
19.1
179.1
19.3
180.5
18.1
180.2
19.0
29.66
1J[560]
27.75
2J[34]
19.0
3J[96]
13.5
4J[n.o.]
17.52
1J[370]
19.12
2J[25]
16.5
3J[n.o.]
13.6
4J[n.o.]
137.5
1J[640]
136.5
2J[50]
128.5
3J[69]
131.0
4J[32]
138.0
1J[650]
136.0
2J[50]
128.0
3J[n.o.]
130.0
4J[n.o.]
1J[600]
8.7
b
g
d
2J[43.5]
7
7
7
7
n
n
aChemicalshifts ( d) in ppm, J(1H-1H) and J[119Sn-1H] in Hz.
bn.o. ¼ not observed.
c

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16
MASOOD ET AL.

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TRI-, DI-, AND CHLORODIORGANOTIN(IV) DERIVATIVES
17
Table VI. 13C NMR Dataa,b,c of Di- and Chlorodiorganotin Carboxylates of HL2
Compound
?
Carbon;
(7)
R ¼ Et
(8)
R ¼ Et
(9)
R ¼ n-Bu
(10)
R ¼ n-Bu
(11)
R ¼ Ph
(12)
R ¼ Ph
2
3
4
5
6
7
8
a
138.6
129.0
127.9
130.8
139.4
116.3
175.8
17.6
134.0
130.0
128.7
131.2
140.0
115.4
176.0
17.9
138.5
128.6
127.9
130.8
139.4
116.4
175.8
25.0
133.0
129.2
128.0
130.4
139.6
115.2
175.6
26.2
138.6
128.9
128.0
130.7
139.4
116.5
175.8
137.6
1J[620]
134.0
2J[48]
134.8
3J[70]
130.0
4J[34]
133.0
129.0
128.0
130.0
139.0
115.0
176.0
137.2
1J[650]
135.2
2J[50]
127.8
3J[69]
131.0
4J[n.o.]
1J[605]
8.8
1J[530]
9.1
1J[560]
26.5
1J[502]
26.6
b
g
d
2J[42]
7
2J[40]
7
2J[33]
26.2
2J[35]
26.2
3J[90]
13.4
3J[93]
13.4
7
7
4J[n.o.]
4J[n.o.]
n
n
aChemicalshifts ( d) in ppm, J(1H-1H) and J[119Sn-1H] in Hz.
bn.o. ¼ not observed.
c
signals in the 13C and 1H spectra. The high electronegativity of tin due to the
1
presence of chloride ion increases the magnitude of the J[119Sn-13C] and
2J[119Sn-1H] coupling constants25. In our compounds, the presence of oxy-
gen and chlorine atoms attached to tin increases its Lewis acidity and fa-
cilitates chelation of the carbonyl oxygen resulting in a trigonal bipyramidal
geometry. Hence, comparison of these coupling constants and tin chemical
shifts with previous data suggests a penta-coordinated state for the tin
atom9,15 (Fig. 2(d)).

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18
MASOOD ET AL.
Figure 2. Suggested structures of the complexes.
Mass Spectrometry
The mass fragmentation data of both series are given in Tables VII-IX.
The molecular ion peaks, as reported earlier9,14, are not observed for most
of the compounds. Generally, in triorganotin derivatives, the major frag-
mentation is the loss of an R group followed by the elimination of CO2. An
alternate route of ragmentation is the loss of ligand anion first, followed by
the loss of successive R groups until Snþ is obtained. For diorganotin di-
carboxylates, the main fragmentation is due to the loss of one ligand which
follows the loss of CO2 and then successive losses of two R groups. Chloro
derivatives follow the same pattern as the triorganotin carboxylates. The
first loss is due to an R group followed by CO2 and then another R group
and some fragments of the ligand.
EXPERIMENTAL
Instrumentation
Melting points were determined in a capillary tube using an electro-
thermalmetling point apparatus ModelMP-D, Mitamura Rikero Kogyo
(Japan) and are uncorrected. Infrared spectra were recorded in KBr pellets
using a Hitachi Model270-50 infrared spectrophotometer. The NMR
spectra were recorded on, Bruker 250ARX spectrometer in CDCl3 using
1
Me4Si as reference for H and 13C and Me4Sn as reference for 119Sn.

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TRI-, DI-, AND CHLORODIORGANOTIN(IV) DERIVATIVES
19
Table VII. Fragmentation Pattern and Relative Abundance (%) of Triorganotin
Carboxylates of HL1
Fragment ion
(1) R ¼ Me
(4) R ¼ n-Bu
(6) R ¼ Ph
[R3SnO2CR0]þ
[R2SnO2CR0]þ
[R3SnR0]þ
[RSnR0]þ
7
10
51
7
100
7
40
30
40
37
7
56
8
21
67
7
38
27
6
4
8
38
7
96
14
66
12
21
100
[R3Sn]þ
[R2Sn]þ
[RSn]þ
[HO2CR0]þ
[SnO2CR0]þ
[C7H5O]
84
Synthesis
Triorganotin Carboxylates (Compounds (1), (4), and (6))
Compounds with the generalformula R SnL1 were prepared by double
3
displacement reaction between AgL1 and R3SnCl[eq (1)] 13,14. The silver salt of
the ligand, AgL1 (3.68 g, 0.01 mole) was suspended in 50 mL dry chloroform in
a 250 mL two-necked round bottom flask equipped with a water-cooled
condenser and a magnetic stirrer. The appropriate triorganotin chloride
(0.01 mole) in 50 mL dry chloroform was added dropwise to the suspension
with constant stirring. The reaction mixture was then refluxed for 678 hours,
cooled to room temperature and allowed to stand overnight at room tem-
perature. AgClformed during the reaction was fitlered off using a conven-
tional Schlenk apparatus. The filtrate was treated with activated charcoal at
50 ꢀC, filtered and the solvent was removed under reduced pressure. The solid
mass obtained was crystallized from a suitable solvent (dichloromethane or n-
hexane). Physicalparameters of these compounds are given in Table I.
Diorganotin Carboxylates (Compounds (2), (3), (5), (7), (9), and (11))
Diorganotin compounds were prepared by the condensation reaction
of the ligand acids, HL and organotin oxide [eq (2)]14. The ligand acid, HL1
(5.22 g) or HL2 (7.22 g, 0.02 mole) and the appropriate organotin oxide
(0.01 mole) were refluxed in 100 mL dry toluene for 476 hours. Water
formed during the reaction was continuously removed using a Dean-Stark
apparatus. Toluene was then removed under reduced pressure with a high

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MASOOD ET AL.
Table VIII. Fragmentation Pattern and Relative Abundance (%) of Diorganotin
Carboxylates of HL1 and HL2
(2)
(3)
(5)
(7)
(9)
(11)
Fragment ion
R ¼ Et R ¼ n-Bu R ¼ Ph R ¼ Et R ¼ n-Bu R ¼ Ph
[R2Sn(O2CR0)2þ]þ
[RSn(O2CR0)2]
[RSn(O2CR0)R0]þ
[RSnR02]þ
[R2SnO2CR0]þ
[R2SnR0]þ
[SnR0]þ
À
68
58
10
38
16
À
À
42
16
20
60
8
À
22
18
11
8
28
10
6
À
85
61
49
14
12
63
79
À
À
84
27
5
11
2
À
30
16
12
31
24
9
6
65
5
[HO2CR0]þ
[R2SnO]þ
18
70
100
À
22
68
84
À
74
À
64
82
À
À
[C7H5O]þ
[SnOH]
[C2H5S]
[C5H5]
À
À
À
100
82
67
100
69
40
76
20
76
À
À
À
À
À
À
vacuum pump. The residue was treated with activated charcoalin 150 mL
dry chloroform and filtered. The filtrate was concentrated and left overnight
at À5 ꢀC. The semisolid/solid mass was crystallized or extracted by using
appropriate solvents (dichloromethane, chloroform or n-hexane). Physical
parameters are given in Table I.
Table IX. Fragmentation Pattern and Relative Abundance (%) of Mono-
chlorodiorganotin Carboxylates of HL2
Fragmentation ion
(8) R ¼ Et
(10) R ¼ n-Bu
(12) R ¼ Ph
[R2Sn(O2CR0)(Cl)]þ
[RSn(O2CR0)(Cl)]þ
[RSn(R0)(Cl)]þ
[SnR0(Cl)]þ
7
16
5
4
2
7
7
7
3
9
6
35
78
9
100
21
7
100
7
8
76
8
28
31
6
65
7
[R2Sn(O2CR0)]þ
[R2Sn(Cl)]þ
[SnR0]þ
3
26
22
7
100
39
[HO2CR0]þ
[C4H3SSn]þ
[Sn-OH]þ
[C5H5]þ

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TRI-, DI-, AND CHLORODIORGANOTIN(IV) DERIVATIVES
21
Chlorodiorganotin Carboxylates (Compounds (8), (10), and (12))
These compounds were prepared according to our previously reported
method [eq (3)]15. Equimolar amounts (100 mmol) of R2SnL2 and R2SnCl2
were refluxed in 100 mL dry chloroform for 678 hours. The reaction mixture
was then concentrated under vacuum and kept at À10 ꢀC for 10715 days.
The semisolid or solid mass thus obtained was purified by repeated ex-
traction with an appropriate solvents mixture (dichloromethane/n-hexane,
1:1). Physicalparameters are given in Tabel I.
ACKNOWLEDGMENTS
Financialsupport for this work from Quaid-I-Azam University is
highly acknowledged. We are thankful to Rhone-Poulenc for providing the
ligand, 3-benzoyl-a-methylphenylacetic acid.
REFERENCES
1. Holmes, R.R.; Schmid, C.G.; Chandrasekhar, V.; Day, R.O.; Holmes,
J.M. Oxo Carboxylate Tin Ladder Cluster. A New Structural Class of
Organotin Compounds. J. Am. Chem. Soc. 1987, 109, 140871414.
2. Valles, P.G.; Peruzzo, V.; Tagliavini, V.; Ganis, P. The Crystal Structure
of Di-m-3-oxo-bis(m-monochloroacetato-O,O0)bis(monochloroacetato)-
tetra-kis[dimethyltin(IV)]. J. Organomet. Chem. 1984, 276, 32579.
3. Tiekink, E.R.T. StructuralChemistry of Organotin Carboxyaltes:
A Review of the Crystallographic Literature. Appl. Organomet.
Chem., 1991, 5, 1723.
4. Danish, M.; Alt, H.G.; Badshah, A.; Ali, S.; Mazhar, M.; Islam, N.
Organotin Esters of 3-(2-Furanyl)-2-propenoic Acid: Their Character-
ization and Biological Activity. J. Organomet. Chem. 1995, 486, 51756.
5. Sandhu, S.K.; Hundal, R.; Tiekink, E.R.T. Structural Chemistry of
Organotin Carboxylates XVII. Diorganotin(IV) Derivatives of N-
Phthaloyl-DL-Valine. J. Organomet. Chem. 1992, 430, 15723.
6. Badshah, A.; Danish, M.; Ali, S.; Mazhar, M.; Mahmood, S. Synthesis
and Characterization of Di- and Triorganotin(IV) Compounds of 3-(2-
Thienyl)-2-propenoic Acid. Synth. React. Inorg. Met.-Org. Chem.
1994, 24, 115571166.
7. Danish, M.; Ali, S.; Mazhar, M.; Badshah, A.; Masood, T.; Tiekink,
E.R.T. Crystal and Molecular Structures of Two Polymeric Triorga-
notin 3-(2-Thienyl)-2-propenoate Derivatives. Main Group Met.
Chem. 1995, 18, 27734.

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MASOOD ET AL.
8. Danish, M.; Ali, S.; Mazhar, M.; Badshah, A.; Tiekink, E.R.T. Crystal
and Molecular Structures of Bis[(3-(2-furanyl)-2-propenoate)di-N-bu-
tyltin]oxide and Triphenyltin 3-(2-Furanyl)-2-propenoate. Main
Group Met. Chem. 1995, 18, 6977705.
9. Danish, M.; Ali, S.; Mazhar, M.; Badshah, A.; Chaudhary, M.I.;
Alt, H.G.; Kehr, G. Mossbauer, Multinuclear Magnetic Resonance
and Mass Spectrometric Studies of Organotin Carboxylates of m-
Methyl-trans-cinnamic Acid. Polyhedron 1995, 14, 311573123.
10. Danish, M.; Ali, S.; Mazhar, M.; Badshah, A. Synthesis and Spectral
Studies of Bis{dialkyl[trans-3-(2-thiophenyl)-2-propenoate]tin}oxide:
CrystalStructure of {[(CH 3)2SnO2C-CH¼CH-C4H3S]O}2. Main
Group Met. Chem. 1996, 19, 1217131.
11. Danish, M.; Badshah, A.; Ali, S.; Mazhar, M.; Islam, N.; Chaudhary,
M.I. Preparation and NMR, Mass and Mossbauer Studies of Di- and
Triorganotin(IV) Derivatives of 3-(2-Furanyl)-2-propenoic Acid. Iran.
J. Chem & Chem. Eng. 1994, 13, 176; Chem. Abstr. 1995, 123, 56081.
12. Danish, M.; Ali, S.; Badshah, A.; Mazhar, M.; Massod, H.; Malik, A.;
1
Kehr, G. H, 13C, 119Sn NMR, 119mSn Mossbauer, Infrared and Mass
Spectrometric Studies of Organotin Carboxylates of 2-[(2,3-Di-
methylphenyl)amino]-benzoic Acid. Their Effect on Microorganism.
Synth. React. Inorg. Met.-Org. Chem. 1997, 7, 8637885.
13. Ali, S.; Danish, M.; Badshah, A.; Mazhar, M.; Rehman, A.; Islam, N.
Synthesis, Characterization and Biological Activity of Organotin De-
rivatives of 3-(2-Furanyl)-2-propenoic Acid and 3-(2-Thienyl)-2-pro-
penoic Acid. J. Chem. Soc. Pak. 1993, 15, 1547156.
14. Gielen, M.; El Khloufi, A.; Biesemans, M.; Kayser, F.; Willem, R.
Diorganotin 2-Fluorocinnamates and 4-Fluorophenylacetates: Synth-
esis, Characterization and in vitro Antitumor Activity. Appl. Orga-
nomet. Chem. 1993, 7, 20176.
15. Ali, S.; Danish, M.; Mazhar, M. Redistribution Reactions of Dior-
ganotindicarboxylates and Diorganotindihalides:
A Convenient
Method for the Preparation of Halo-diorganotincarboxylates. Het-
eroatom Chem. 1997, 3, 2737278.
16. Wrackmeyer, B.; Vollrath, H.; Ali, S. Spirocyclic Stannole Derivatives
by 1,1-Organoboration of 2,2-Bis(1-alkynyl)-1,3-di-tert-butyl-1,3,2-
diaza-stannacyclohexanes. Inorg. Chim. Acta. 1999, 296, 26732.
17. (a) Molloy, K.C.; Quill, K.; Nowell, I.W. Organotin Biocides. Part 8.
The CrystalStructure of Triphenytiln Formate and Comparative
Variable-temperature Tin-119 Mossbauer Spectroscopic Study of Or-
ganotin Formate and Acetates. J. Chem. Soc. Dalton Trans. 1987,
1017106; (b) Molloy, K.C. Biorganotin Compounds in Hartley, F.R.

ORDER
REPRINTS
TRI-, DI-, AND CHLORODIORGANOTIN(IV) DERIVATIVES
23
Ed., The Chemistry of the Metal-Carbon Bond, John Willey: New
York, 1989; 5, 465.
18. (a) Kalinowski, H.O.; Berger, S.; Brown, S. 13C NMR Specktrosckopie;
Thieme Verlag: Stuttgart, Germany, 1984; (b) Ballico, E.; Floris, B.
Metalation of Alkynes. Part 9. Substituent Effect in Acetox-
ymercuration of Arylphenylethynes. Main Group Met. Chem. 1998,
21, 5277542.
19. Dolling, K.; Krug, A.; Hartung, H.; Weichman, H. C-Stannylmethy-
lated N-Acetyl- and N-Formyl-aminomalonic Acid Derivatives Z.
Anorg. Allg. Chem. 1995, 621, 63771.
20. Wrackmeyer, B.; Kehr, G.; Sub, J. 1,1-Organoboration of Di-1-alky-
nylsilanes with Alkynyl Groups of Different Reactivity: New Orga-
nometallis-Substituted Siloles. Chem. Ber. 1993, 126, 222176.
21. Lockhart, T.P.; Menders, W.F.; Holt, E.M. Solution and Solid-state
Molecular Structures of Me2Sn(OAc)2 and its Hydrolyzate, ([Me2-
Sn(OAc)]2O)2, by Solution and Solid-state Carbon-13 NMR. X-Ray
Difffraction Study of the Hydrolyzate. J. Am. Chem. Soc. 1986, 108,
6611716.
22. (a) Holecek, J.; Lycka, A. Dependence of [1J(tin-119-carbon-13)] on
the Carbon-Tin-Carbon Angle in Butyltin(IV) Compounds. Inorg.
Chim. Acta 1986, 118, L157L16; (b) Holecek, J.; Handller, K.; Nad-
vornik, M.; Lycka, A. Dependence of [1J(tin-119-carbon-13)] on the
Mean Carbon-Tin-Carbon Angle in Phenyltin(IV) Compounds. Z.
Chem. 1990, 30, 26576.
23. Tahir, M.N.; Ulku, D.; Ali, S.; Masood, M. T.; Danish, M.;
Mazhar, M. (Ketoprofenato)trimethyltin(IV). Acta Cryst. 1997 C53,
157471576.
24. Parvez, M.; Ali, S.; Masood, M. T.; Mazhar, M.; Danish, M. Diethyl
Bis[3-(2-thiophenyl)-2-propenoate-O,O0]tin(IV). Acta Cryst. 1997,
C53, 121171213.
25. Wrackmeyer, B.; Kehr, G. Tetra-1-alkynyltin Compounds and Ex-
change Reactions with Tin Tetrachloride. 13C and 119Sn Nuclear
Magnetic Resonance Study. Main Group Met. Chem. 1993, 16,
305714.
Received January 5, 2000
Accepted September 23, 2001
Referee I: K. Moedritzer
Referee II: M. K. Denk

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