Synthesis, crystal structure, and transesterification reaction of the β-propoxycarbonylethyltin trichloride complex with dibenzylsulfoxide

Article abstract of DOI:10.1081/SIM-100001939

Synthesis, crystal structure and transesterification reaction of the β-propoxy-carbonylethyltin trichloride complex with dibenzylsulfoxide have been reported and a possible mechanism for the transesterification has been suggested. A series of the complexes of β-alkoxycarbonylethyltin trichloride with dibenzylsulfoxide have been synthesized and characterized by means of elemental analyses, IR, and ¹H NMR spectra.

Full text of DOI:10.1081/SIM-100001939

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SYNTHESIS, CRYSTAL STRUCTURE, AND
TRANSESTERIFICATION REACTION OF THE β-
PROPOXYCARBONYLETHYLTIN TRICHLORIDE COMPLEX
WITH DIBENZYLSULFOXIDE
Laijin Tian a , Bin Zhao a & Feng Li a
a Department of Chemistry , Qufu Normal University , Qufu, Shandong, 273165, People's
Republic of China
Published online: 20 Aug 2006.
To cite this article: Laijin Tian , Bin Zhao & Feng Li (2001) SYNTHESIS, CRYSTAL STRUCTURE, AND TRANSESTERIFICATION
REACTION OF THE β-PROPOXYCARBONYLETHYLTIN TRICHLORIDE COMPLEX WITH DIBENZYLSULFOXIDE, Synthesis and
Reactivity in Inorganic and Metal-Organic Chemistry, 31:1, 139-148, DOI: 10.1081/SIM-100001939
To link to this article: http://dx.doi.org/10.1081/SIM-100001939
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SYNTH. REACT. INORG. MET.-ORG. CHEM., 31(1), 139–148 (2001)
SYNTHESIS, CRYSTAL STRUCTURE, AND
TRANSESTERIFICATION REACTION OF
THE β-PROPOXYCARBONYLETHYLTIN
TRICHLORIDE COMPLEX WITH
DIBENZYLSULFOXIDE
Laijin Tian,∗ Bin Zhao, and Feng Li
Department of Chemistry, Qufu Normal University, Qufu,
Shandong 273165, People’s Republic of China
ABSTRACT
Synthesis, crystal structure and transesterification reaction
of the β-propoxy-carbonylethyltin trichloride complex with diben-
zylsulfoxide have been reported and a possible mechanism for the
transesterification has been suggested. A series of the complexes of
β-alkoxycarbonylethyltin trichloride with dibenzylsulfoxide have
been synthesized and characterized by means of elemental analy-
ses, IR, and 1H NMR spectra.
INTRODUCTION
β-Alkoxycarbonylethyltin trichlorides, the so-called estertin chlorides, have
attracted considerable attention ever since their syntheses were first reported
(1–10). Their complexes with neutral and ligand anions have been investigated
∗Corresponding author. E-mail: zhaobinl@ji-public.sd.cninfo.net
139
Copyright ꢀ 2001 by Marcel Dekker, Inc.
www.dekker.com
C

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TIAN, ZHAO, AND LI
extensively (2–9). However, less attention has been paid to the transesterifications
of their complexes with neutral ligands (10). In this paper, we report the synthesis,
crystal structure and transesterification reaction of the β-propoxycarbonylethyltin
trichloride complex with dibenzylsulfoxide.
RESULTS AND DISCUSSION
The synthesis and transesterification reaction of β-propoxycarbonylethyltin
trichloride complex with dibenzylsulfoxide (L) may be represented by the follow-
ing equations:
n-PrOCOCH2CH2SnCl3 + L → n-PrOCOCH2CH2SnCl3·L
(1)
n-PrOCOCH2CH2SnCl3·L + ROH → ROCOCH2CH2SnCl3·L + n-PrOH
(1)
(2)-(10)
R = Me (2), Et (3), i-Pr (4), allyl (5), n-Bu (6), i-Bu (7),
n-amyl (8), i-amyl (9), cyclohexyl (10)
The physical and analytical data of these complexes are listed in Table 1. They
are colorless crystals and air-stable and soluble in benzene and in common polar
organic solvents, such as ethanol, chloroform, acetone and nitrobenzene, but in-
soluble in the saturated hydrocarbons as hexane and petroleum ether. The molar
conductance values (4.8–7.2 S cm2 mol−1) of the complexes in nitrobenzene at
room temperature suggest that they are non-electrolytes (11).
Infrared Spectra
The characteristic IR bands of the complexes are listed in Table 2. The
ν(C O) values of the complexes (1634–1650 cm−1) exhibit a remarkable red-shift
=
fromthatofthefreefattyacidester(ca. 1740cm−1). Thisindicatesthatthecarbonyl
oxygen is coordinated intramolecularly to the−t1in atom (3,12). Compared with
=
=
ν(S O) of the free dibenzylsulfoxide (1028 cm ), the ν(S O) frequency of these
complexes shifts to lower frequency (945–962 cm−1), confirming its coordination
tothetinviaoxygen(13). TheSn ← Ostretchingvibrationisexpectedintheregion
(14,15) below 400 cm−1 and cannot be obtained using KBr disks. In chloroform
=
=
solution, the ν(C O) and ν(S O) bands of the complexes are in the 1650–1660
and950–966cm−1 regions, respectively. Thus, itmaybeseenthatallthecomplexes
are six-coordinated to tin in the solid and in solution. Their structures are suggested
in Figure 1.

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141
Table 1. Physical and Analytical Data for the Compounds
Analysis, Found (Calculated)
Compd. Empirical Formula Yield m.p.
No.
(Formula Weight) (%)
(◦C)
C
H
S
Sn
(1)
C20H25Cl3O3SSn
(570.51)
C18H21Cl3O3SSn
(542.47)
C19H23Cl3O3SSn
(556.49)
C20H25Cl3O3SSn
(570.51)
C20H23Cl3O3SSn
(568.50)
C21H27Cl3O3SSn
(584.55)
C21H27Cl3O3SSn
(584.55)
C22H29Cl3O3SSn
(598.57)
87 125–6 42.28
4.32
(4.42)
3.76
(3.90)
4.06
(4.17)
4.19
(4.42)
4.06
(4.08)
4.47
(4.66)
4.48
(4.66)
4.89
(4.88)
4.63
(4.88)
4.76
(4.79)
5.49
(5.62)
5.94
(5.91)
5.68
(5.76)
5.57
(5.62)
5.66
(5.64)
5.33
(5.49)
5.51
(5.49)
5.32
(5.36)
5.35
(5.36)
5.30
(5.25)
20.57
(42.10)
150 39.87
(39.85)
79 123–4 41.03
(41.01)
(20.81)
21.84
(21.88)
21.28
(21.33)
20.68
(20.81)
20.62
(20.88)
20.42
(20.31)
20.05
(20.31)
19.77
(19.83)
19.52
(19.83)
19.08
(19.44)
(2)
(3)
(4)
(5)
(6)
(7)
(8)
(9)
(10)
89
63 146–8 42.08
(42.10)
84 113–4 42.13
(42.25)
117 43.09
(43.15)
76 120–1 42.96
(43.15)
124 44.08
(44.14)
98–9 43.85
(44.14)
172 45.15
(45.24)
80
78
76
68
C22H29Cl3O3SSn
(598.57)
C23H29Cl3O3SSn
(610.58)
Table 2. IR Spectral Data (cm−1) for the Compoundsa
–
–
=
=
Compd.
ν(C O)
ν(C O)
ν(S O)
ν(Sn C)
(1)
(2)
(3)
(4)
(5)
(6)
(7)
(8)
(9)
(10)
1638 vs
1649 vs
1642 vs
1636 vs
1639 vs
1640 vs
1648 vs
1634 vs
1634 vs
1650 vs
1226 s
1236 s
1248 s
1231 s
1222 s
1221 s
1244 s
1232 s
1230 s
1233 s
960 vs
959 vs
945 vs
962 vs
945 vs
950 vs
950 vs
948 vs
946 vs
950 vs
480 w
475 w
477 w
480 w
482 w
470 w
475 w
480 w
482 w
478 w
avs = very strong, s = strong, w = weak.

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142
TIAN, ZHAO, AND LI
Cl
CH2
Cl
Cl
H2C
C
Sn
O
RO
O
S
C6H5CH2
CH2C6H5
Figure 1. Suggested structures of the complexes.
1H NMR Spectra
1
The H NMR date of the β-alkoxycarbonylethyltin trichloride complexes
with dibenzylsulfoxide in deuterochloroform are given in Table 3. These com-
plexes exhibit two triplets centered at 2.64–2.74 and 1.78–1.84 ppm attributable to
COCH2 and CH2Sn protons, respectively. The evidence of carbonyl group oxygen
to tin coordination in these complexes is also obtained from the chemical shift val-
ues of the CHnO (n = 1–3) protons of the alkoxyl group of the ester group. These
proton signals show a downfield shift compared to those of the free fatty acid ester
since coordination causes a deshielding effect on the CHnO (n = 1–3) protons by
the electron distribution (1,6,10). Compared with δ (CH2S) of the free dibenzylsul-
foxide (4.00 ppm), the protons in these complexes show a marked downfield shift
=
(ꢀδ = ∼0.10 ppm) due to coordination of S O with the tin atom thus decreasing
the electron shielding of the CH2S protons.
Table 3. 1H NMR (δ, CDCl3) Spectral Data for the Compoundsa
Compd. CHnO (n = 1 − 3)
COCH2
CH2Sn
CH2S
(1)
(2)
(3)
(4)
(5)
(6)
(7)
(8)
(9)
(10)
4.23 (t, 6.6)
3.88 (s)
2.70 (t, 7.5) 1.82 (t, 7.4) 4.11 (s)
2.70 (t, 7.6) 1.83 (t, 7.6) 4.10 (s)
2.68 (t, 7.5) 1.81 (t, 7.5) 4.10 (s)
2.65 (t, 7.2) 1.79 (t, 7.2) 4.10 (s)
2.68 (t, 7.5) 1.78 (t, 7.0) 4.12 (s)
2.69 (t, 7.8) 1.81 (t, 7.6) 4.11 (s)
2.74 (t, 7.5) 1.84 (t, 7.8) 4.10 (s)
2.69 (t, 7.5) 1.80 (t, 7.5) 4.11 (s)
2.70 (t, 7.6) 1.83 (t, 7.6) 4.10 (s)
2.64 (t, 7.2) 1.78(t, 7.2) 4.10 (s)
4.33 (q, 7.0)
5.09 (m, 6.2)
4.74 (d, 5.6)
4.27 (t, 6.8)
4.02 (d, 6.4)
4.26 (t, 6.8)
4.31 (t, 6.8)
5.02 (m, 4.4)
aThe numbers in parentheses are the coupling constants in Hz.
d: Doublet; m: Multiplet; q = Quartet, s = Singlet, t = Triplet.

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ESTERTIN CHLORIDE COMPLEXES
143
C(19)
C(20)
O(3)
C(17)
C(16)
C(15)
C(18)
C(5)
C(6)
Cl(1)
C(4)
O(2)
Sn(1)
C(7)
C(3)
Cl(2)
S(1)
C(2)
Cl(3)
O(1)
C(1)
C(8)
C(10)
C(9)
C(11)
C(14)
C(13)
C(12)
Figure 2. Molecular structure of (1).
Crystal Structure of n-PrOCOCH2CH2SnCl3·L (1)
The molecular geometry and the atomic numbering scheme for (1) are
shown in Figure 2. The selected bond lengths and bond angles are given in
Table 4.
The complex exists as a discrete molecule which contains a five-membered
chelate ring, formed via carbonyl oxygen to tin coordination. The tin atom is
six-coordinated with the coordinating atoms Cl(1), Cl(2), Cl(3), O(1), O(2), and
–
–
C(15) in a distorted octahedral arrangement. The bond angles Cl(1) Sn(1) O(1),
Cl(2)−Sn(1)−O(2), and Cl(3)−Sn(1)−C(15) are, respectively, 170.5(1), 175.6(1),
and158.8(2)◦, whichareveryclosetothoseofreportedforROCOCH2CH2SnCl3·D
❛
–
(D is an oxygen donor) (8,16). The Sn(1) O(2) distance (2.343(7) A) in complex
–
(1) is comparable with the intramolecular Sn O distances in other six-coordinated
❛
–
–
ROCOCH2CH2Sn compounds (Sn O, 2.33–2.44 A) (8,9,16). As expected, the
Sn(1) O(1) (2.188(4) A) and Sn(1) O(2) distances are both longer than the sum
(2.06 A) of the covalent radii of tin and oxygen and shorter than the sum (3.70
A) of the Van der Waals’ radii. The bond length Sn(1) O(2) is longer than that
❛
–
❛
❛
–

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TIAN, ZHAO, AND LI
❛
Table 4. Selected Bond Lengths (A) and Bond Angle (◦) for (1)
Bond Length
–
–
Sn(1) Cl(1)
2.452(3)
2.387(3)
2.368(3)
2.188(4)
2.343(7)
2.129(7)
1.521(4)
1.809(7)
1.835(6)
C(1) C(2)
1.504(9)
1.494(9)
1.513(11)
1.92(12)
1.189(9)
1.309(10)
1.440(11)
1.493(15)
1.346(17)
–
–
Sn(1) Cl(2)
C(8) C(9)
–
–
C(15) C(16)
C(16) (17)
–
C(17) O(2)
C(17) O(3)
–
O(3) C(18)
C(18) C(19)
–
C(19) C(20)
Sn(1) Cl(3)
–
–
Sn(1) O(1)
–
Sn(1) O(2)
–
–
Sn(1) C(15)
–
–
–
S(1) 0(1)
S(1) C(1)
S(1) C(8)
–
Bond Angles
–
–
–
–
–
–
–
–
–
–
–
–
–
–
–
–
–
–
Cl(1) Sn(1) Cl(2)
96.2(1)
88.8(1)
170.5(1)
88.2(1)
94.6(2)
96.5(1)
90.8(1)
175.6(1)
103.9(2)
84.1(1)
Sn(1) O(1) S(1)
123.9(3)
–
– –
Cl(1) Sn(1) Cl(3)
Sn(1) C(15) C(16) 108.7(5)
–
–
–
Cl(1) Sn(1) (1)
Sn(1) O(2) C(17)
110.8(5)
101.8(3)
105.6(3)
100.8(3)
108.1(4)
114.5(5)
–
– –
Cl(1) Sn(1) O(2)
O(1) S(1) C(1)
–
– –
O(1) S(1) C(8)
Cl(1) Sn(1) C(15)
–
– –
Cl(2) Sn(1) Cl(3)
C(1) S(1) C(8)
–
– –
S(1) C(1) C(2)
Cl(2) Sn(1) O(1)
–
– –
Cl(2) Sn(1) O(2)
S(1) C(8) C(9)
–
– –
Cl(2) Sn(1) C(15)
C(15) C(16) C(17) 113.4(6)
–
–
–
Cl(3) Sn(1) O(1)
O(2) C(17) C(16)
122.2(7)
125.2(8)
112.6(7)
116.5(9)
117.8(6)
–
– –
Cl(3) Sn(1) O(2)
83.11(1) O(2) C(17) O(3)
–
–
– –
O(3) C(17) C(16)
Cl(3) Sn(1) (1) C(15) 158.8(2)
–
– –
O(1) Sn(1) O(2)
84.8(2)
89.9(3)
76.1(3)
O(3) C(18) C(19)
–
– –
C(17) O(3) C(18)
– –
C(18) C(19) C(20) 110.9(10)
O(1) Sn(1) C(15)
–
O(2) Sn(1) C(15)
–
of Sn(1) O(1), and shows that carbonyl O(2) coordination to tin is weaker than
sulfinyl O(1) coordination.
Transesterification of (1)
When the β-propoxycarbonylethyltin trichloride complex with dibenzyl-
sulfoxide is refluxed in an alcohol, it is readily converted into the corresponding
alkoxycarbonyl analogs with yields of 63–89%.We attribute the occurrence of
this novel transesterification to intramolecular Lewis acid catalysis by the elec-
trophilic SnCl3 group. The coordination of the ester carbonyl oxygen to the tin
atom polarized the carbonyl bond, thereby making the carbonyl carbon more sus-
ceptible to attack by a nucleophilic reagent such as an alcohol. A possible mecha-
nism for the transesterification is suggested in the Figure 3. The transesterification

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ESTERTIN CHLORIDE COMPLEXES
145
CH2
C
CH2
CH2
C
CH2
ROH
+
−
.
.
n Pro
n Pro
O
O
SnCl3 L
n Pro
O
O
SnCl3 L
CH2
C
CH2
CH2
C
CH2
n PrOH
+
−
−
.
.
SnCl3
L
n Pro
SnCl3 L
+
OR
ROH
H
CH2
C
CH2
CH2
C
CH2
+
RO
−
.
.
O
SnCl3
L
O
SnCl3 L
RO
Figure 3. Proposed mechanism for the transesterification of (1).
provided a convenient way for preparing the β-alkoxycarbonylethyltin trichloride
complexes.
EXPERIMENTAL
Materials and Physical Measurements
All chemicals were of reagent grade and were used without further purifica-
tion. β-Propoxycarbonylethyltin trichloride and dibenzylsulfoxide were prepared
according to leterature methods (6,17). Carbon, hydrogen, nitrogen, and sulfur
analyses were obtained using a Perkin Elmer 2400 Series II elemental analyser,
and tin was determined titrimetrically as Sn2+. Melting points were measured on
a TX4-100A microscopic melting point apparatus. IR spectra were recorded on
an Alpha Centauri FT-IR spectrophotometer using KBr discs in the range 4000–
400 cm−1. 1H NMR spectral data were collected using a Bruker AC-80 spectrome-
ter or a Varian Unity-400 spectrometer with CDCl3 as solvent and TMS as internal
standard.
Synthesis of n-PrOCOCH2CH2SnCl3·L (1)
A solution of dibenzylsulfoxide (L) (1.15 g, 5 m mol) dissolved in ben-
zene (30 mL) was added dropwise to a stirred solution of β-propoxycarbonyl-
ethyltintrichloride (1.70 g, 5 m mol) in benzene(30 mL), and the mixture was

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TIAN, ZHAO, AND LI
refluxed for an hour and concentrated to ca. 20 mL by evaporation under reduced
pressure. The colorless crystals of (1) formed in the solution were filtered and
recrystallized from benzene–petroleum ether (b.p. 60–90◦C) (1:1, v/v) and dried
in vacuo. Yield is 2.48 g.
Transesterification of n-PrOCOCH2CH2SnCl3·L(1)
A solution of (1) (2.85 g, 5 m mol) dissolved in 60 mL ROH was refluxed
for 2 h, and then concentrated slowly to ca. 15 mL by evaporation under reduced
pressure. The resultant white solid was recrystallized from benzene–petroleum
ether (b.p. 60–90◦C) (1:1, v/v) and dried in vacuo. The yields and melting points
of the obtained compounds are shown in Table 1.
Crystal Structure Determination for (1)
A colorless crystal with dimensions 0.15 × 0.26 × 0.58 mm was used for
the single crystal determination. Data were collected on a Nicolet R3m/E four-
❛
circle diffractometer with graphite monochromated Mo Kα radiation (0.71073 A),
using the θ/2θ scan technique (2.2 ≤ θ ≤ 25.0◦). 2516 independent reflections
were measured of which 2250 had I > 2.0σ(I) and were considered to be ob-
served. The data were corrected for Lorentz and polarization factors but not for
absorption. Thecrystalparameterswereasfollows:C20H25Cl3O3SSn, M = 570.5,
❛
orthorhombic, space group P212121, a = 10.62(1), b = 14.27(2), c = 16.35(1) A,
❛
V = 2477.8(3) A3, Z = 4,
Dc = 1.44 Mgm−3, F(000) = 1084, µ(MoKα) =
❛
1.451 mm−1, λ = 0.71073 A, T = 298(2) K.
The structure was solved by the SHELXS-86 program (18) and full-matrix
least-squaresrefinementon F2 wasperformedusingSHELXL-93(19). Anisotropic
displacement parameters were employed for non-H atoms and H-atoms were in-
cluded in the model at their calculated positions and refined isotropically. The
refinement converged to a final R = 0.0336, wR = 0.0382 and goodness-of-fit =
1.04. The maximum and mnimum residual electron density peaks in the final dif-
❛
ference map were 0.552 and −0.470 e A−3, respectively. All calculations were
performed on an Eclipse S/140 computer using the SHELXTL program (20).
ACKNOWLEDGMENT
This work was supported by the State Key Laboratory of Crystal Materials
and the Natural Science Foundation of Shandong Province.

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Received June 28, 2000
Referee I: M. K. Denk
Accepted November 10, 2000
Referee II: J. C. Cochran

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