Lithiation of the tin-containing sulfone Me3SnCH2CH2CH2SO2C6H4CH3-4

Article abstract of DOI:10.1023/A:1013197403154

The tin-containing sulfide Me₃Sn(CH₂)₃-S-C₆H₅CH ₃-4 obtained by photoaddition of 4-toluenethiol to allyltrimethyltin was oxidized with hydrogen peroxide to synthesize the tin-containing sulfone Me₃Sn(CH₂)₃-SO₂-C₆H₄ CH₃-4, the tin and sulfur atoms in which are separated by a trimethylene bribge. Treatment of the sulfone with butyllithium gave a first tin-containing lithium salt having a red-brown color. The exchange reaction of this salt with methyl iodide resulted in formation of two new isomeric tin-containing sulfones Me₃SnCH₂CH₂CH(CH₃)-SO₂-C₆H₄CH₃ and Me₃Sn(CH₂)₃-SO₂-C₆H₄ CH₂CH₃ identified by ¹H NMR spectroscopy. The latter result implies that the tin-containing sulfone is lithiated both by the methylene group adjacent to the sulfonyl group and by the toluene methyl group.

Full text of DOI:10.1023/A:1013197403154

Russian Journal of General Chemistry, Vol. 71, No. 7, 2001, pp. 1041 1044. Translated from Zhurnal Obshchei Khimii, Vol. 71, No. 7, 2001,
pp. 1106 1109.
Original Russian Text Copyright
2001 by Shcherbakov, Stolyarova, Kurskii, Grigor’eva.
Lithiation of the Tin-containing Sulfone
Me3SnCH2CH2CH2SO2C6H4CH3-4
V. I. Shcherbakov, N. E. Stolyarova, Yu. A. Kurskii, and I. K. Grigor’eva
Razuvaev Institute of Organometallic Chemistry, Russian Academy of Sciences, Nizhni Novgorod, Russia
Received April 17, 2000
Abstract The tin-containing sulfide Me3Sn(CH2)3 S C6H5CH3-4 obtained by photoaddition of 4-toluene-
thiol to allyltrimethyltin was oxidized with hydrogen peroxide to synthesize the tin-containing sulfone
Me3Sn(CH2)3 SO2 C6H4CH3-4, the tin and sulfur atoms in which are separated by a trimethylene bribge.
Treatment of the sulfone with butyllithium gave a first tin-containing lithium salt having a red-brown
color. The exchange reaction of this salt with methyl iodide resulted in formation of two new isomeric tin-
containing sulfones Me3SnCH2CH2CH(CH3) SO2 C6H4CH3 and Me3Sn(CH2)3 SO2 C6H4CH2CH3 identified
1
by H NMR spectroscopy. The latter result implies that the tin-containing sulfone is lithiated both by the
methylene group adjacent to the sulfonyl group and by the toluene methyl group.
Sulfones RCH2 SO2 R of the aliphatic (R = R =
Alk) or aliphatic aromatic series (R = Alk, R = Ar)
are CH acids, since their -methylene protons are aci-
dified by the ajacent electron-acceptor SO2 group.
Under the action of alkalis, alkali metal alkoxides and
Me-4. The addition of thiols to trimethylvinyltin occurs
in a more complicated fashion (by and against Mar-
kovnikov’s rule), yielding a mixture two isomeric
organotin sulfides pentyl 2-(trimethylstannyl)ethyl
sulfide Me3SnCH2CH2SC5H11 (III) and pentyl 1-(tri-
methylstannyl)sulfide Me3SnCH(CH3)SC5H11 (IV).
We failed to separate sulfides III and IV by usual
hydrides, butyllithium, or Grignard reagents they form
+
sulfonyl carbanions as salts RCH SO2 RM which are
1
methods and idenfied them as a mixture by H and
stable at room temperature [1 3]. In our previous
study on carbofunctional organotin compounds [4]
we synthesized the organometallic sulfone Me3
Sn(CH2)3 SO2 C5H11. In the present work we set
ourselves the task to prepare first lithium salts of such
sulfones that could further be used as key compounds
for extending the synthetic potential of organometallic
chemistry. For the example we took the tin-containing
aliphatic aromatic sulfone 4-methylphenyl 3-(tri-
methylstannyl)propyl sulfone Me3Sn(CH2)3 SO2
C6H4CH3-4 (I). In this compound the tin and sulfur
atoms are separated by a trimethylene bridge but
equally interesting would be the related derivative
with the shorter dimethylene bridge.
13C NMR spectroscopy. The ratio of the sulfides in
the mixture was found to be 5:1. In addition, three
by-products were isolated and identified: 1,1-bis(tri-
methylstannyl)ethane (Me3Sn)2CHCH3 (V), 1,2-bis-
(trimethylstannyl)ethane Me3SnCH2CH2SnMe3 (VI),
and 1,2-bis(1-penthylthio)ethane C5H11SCH2CH2S
C5H11 (VII). The isomeric organotin compounds V
and VI could also not be separated and were identified
1
as a mixture by H NMR spectroscopy. The ratio of
V and VI is 4:1. The composition of products III
VII can be explained by the scheme proposed in [5].
Sulfides are characteristically readily susceptible
to oxidative imination with sodium N-chloroarene-
sulfonamides Cl(Na)NSO2Ar (Chloramine-T, where
Ar = C6H4Me; Chloramine-XB, where Ar = C6H4Cl,
etc.) to form sulfonimides. Sulfonimides readily
crystallize. They have well-defined melting points and
are used for identification of various silfides [6].
Earlier [7] we employed this reaction for characteriza-
tion of the organotin sulfide Me3Sn(CH2)3SC5H11 and
obtained the first representative of tin-containing sul-
fonimides, Me3Sn(CH2)3S(=NSO2C6H4Cl-4)C5H11. In
the present work sulfide II was characterized in a
similar way as S-(4-methylphenyl)-S-[3-(trimethyl-
Compound I was prepared by oxidation of 4-me-
thylphenyl
3-(trimethylstannyl)propyl
sulfide
Me3Sn(CH2)3 S C6H4CH3-4 (II) with hydrogen
peroxide. Sulfide II, as well as pentyl 2-(trimethyl-
stannyl)ethyl sulfide Me3Sn(CH2)2 S C5H11 which
has a dimethylene bridge between tin and sulfur, were
synthesized in a similar way by photoaddition of the
corresponding thiol to allyltrimethyltin or trimethyl-
vinyltin [4]. The addition of thiols to allyltrimethyltin
occurs stereoselectively to give the target product II
with an admixture of the disulfide 4-MeC6H4SSC6H4
1070-3632/01/7107-1041$25.00 2001 MAIK Nauka/Interperiodica

1042
SHCHERBAKOV et al.
stannyl)propyl]-N-(4-chlorophenylsolfonyl)sulfon-
imide Me3Sn(CH2)3S(=NSO2C6H4Cl-4)C6H4CH3-4
(VIII). By treatment with Chloramine-XB on the mix-
ture of sulfides III and IV we expected to obtain two
isomeric sulfonimides which could further be separa-
ted. But it proved that tin-containing sulfonimides in
which the trialkylstannyl and sulfonyl groups are
intervened by a dimethylene bridge are rather unstable
and undergo ethylene elimination on usual workup.
and to sulfone I. Furthermore, the signals of the
C6H4CH3 group are common for product Xa and
sulfone I. According to calculations, the Xa:X isomer
ratio is 1.6.
EXPERIMENTAL
The IR spectra were recorded on a Perkin Elmer-
577 instrument (neat liquid or suspension in Vaseline
oil; KBr). The 1H and 13C NMR spectra were
measured on a Bruker DPX-200 instrument, internal
reference TMS.
It was found that sulfone I reacts with butyllithium
in DMSO at room temperature to give lithium salt IX
as an abundant brick-red precipitate. The exchange re-
action of the salt with methyl iodide occurs at room
temperature; decoloration is observed immediately
after mixing the reactants. We found that the reaction
product X is a mixture of the isomers 1-methyl
4-methylphenyl 3-(trimethylstannyl)propyl sulfone
(Xa) and 4-ethylphenyl 3-(trimethylstannyl)propyl
sulfone (Xb). This result implies that sulfone I is
lithiated both by a methylene group of the trime-
thylene bridge and by the methyl group attached to
the aromatic ring, resulting in formation of lithium
salts IXa and IXb. The formation of isomer IXb can
be explained by activation of the methyl protons by
the SO2 group through the conjugation system of the
aromatic ring.
Technical grade Chloramine-XB was purified and
its analysis for active chlorine was performed as
described in [8]. Dimethyl sulfoxide was dried in the
following way: 30 ml of DMSO distilled over gra-
nulated NaOH [bp 81 85 C (18 mm)] was treated
with 10 ml of a 0.6 N solution of butyllithium in
hexane, and the resulting mixture was repeatedly dist-
illed collecting DMSO directly into the reaction
ampule [bp 61 62 C (3 mm)]. The other solvents
were purified by conventional procedures. All reac-
tions were carried out in evacuated vessels. Photorea-
ctions were performed under irradiation with a PRK-4
lamp. Thin-layer chromatography was performed on
Silufol UV-254 plates, eluent carbon tetrachloride
acetone (7:1), development in iodine vapor. Analysis
for sulfur in the presence of halogen in VIII was
performed by Schoeniger.
Me3SnCH2CH2CH2 SO2 C6H4CH3-4
BuLi
Me3SnCH2CH2CH SO2 C6H4CH3-4
BuH
4-Methylphenyl 3-(trimethylstannyl)propyl
sulfide (II). A mixture of 12.41 g of allyltrimethyltin,
9.69 g of 4-toluenethiol, and 0.124 g of benzoyl
peroxide in a 70 ml of dry hexane was placed into a
quartz vessel and subjected to UV irradiation for 15 h
with stirring and cooling ( 50 to 70 C). The solvent
was removed at reduced pressure and room tempera-
ture and then evacuated at 100 C for some hours to
remove excess thiol. The residue was distilled in a
vacuum to obtain two fractions. The first fraction was
sulfide II, 13.2 g (66%), bp 138 140 C (1 mm); nD20
Li
IXa
+ Me3SnCH2CH2CH2 SO2 C6H4(CH2Li)-4
IXb
MeI
Me3SnCH2CH2CH SO2 C6H4CH3-4
LiI
Me
Xa
+ Me3SnCH2CH2CH2 SO2 C6H4(CH2CH3)-4.
1
1.5582. IR spectrum, , cm : 760 (SnMe), 705
Xb
1
(CSC), 520 (SnC). H NMR spectrum (CDCl3),
,
We failed to separate isomers Xa and Xb by
vacuum distillation and column chromatography on
SiO2. Thin-layer chromatography, too, gave two
poorly resolved spots. Therefore, the isomers were
ppm (J, Hz): 0.04 s (9H, Me3Sn), d [Me3Sn,
J(117Sn H) 51.6, J(119Sn H) 52.6], 0.89 m (2H,
SnCH2), 1.78 m (2H, CH2CH2CH2), 2.30 s (3H,
C6H4CH3-4), 2.84 m (2H, CH2S), 7.06 7.24 (AA BB
1
identified as a mixture by H NMR, and their ratio
system; 4H, C6H4Me-4). 13C NMR spectrum (CDCl3),
C, ppm (J, Hz): 10.4 (3C, Me3Sn), d [Me3Sn,
1J(117Sn C) 308.8, 1J(119Sn C) 323.3], 10.1
was established by the integral intensities of the
following signals: CH2SO2 (3.07 ppm) and MeCHSO2
(2.90 ppm) multiplets, C6H4CH2Me quartet
(2.75 ppm), and C6H4CH3 singlet (2.45 ppm). As
follows from 1H NMR data, the reaction mixture
contains some starting sulfone I. Therefore, the sig-
nals of the CH2SO2 group belong both to product Vb
1
1
(SnCH2), d [SnCH2, J(117Sn C) 334.7, J(119Sn C)
349.8], 20.9 (C6H4CH3-4), 26.6 (CH2CH2CH2), 38.3
(CH2S), 129.5 (o-CH, C6H4), 129.8 (m-CH, C6H4),
133.1 (p-CH, C6H4), 135.6 (C S, SC6H4). Found, %:
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LITHIATION OF THE TIN-CONTAINING SULFONE Me3SnCH2CH2CH2SO2C6H4CH3-4
1043
C 47.74; H 6.80; S 9.67; Sn 35.68. C13H22SSn. Cal-
culated, %: C 47.46; H 6.69; S 9.74; Sn 36.11. The
second fraction [150 156 C (1 mm)] was allowed to
crystallize and then recrystallized from 15 ml of
pentane ( 10 C) to obtain 0.76 g (8% per thiol II) of
4-methylphenyl disulfide, mp 45 46 C (mp 46 C [9]).
C2H5), 31.6 (SCH2C4H9), 39.1 (SnCH2CH2S).
Me3SnCH(CH3)SCH2CH2CH2CH2CH3 (IV). 1H NMR
spectrum (CDCl3), , ppm (J, Hz): 0.14 s [(CH3)3Sn,
3
2J(H 117/119Sn) 51.5/53.7], 1.46 d [SnCH(CH3)S, J
3
7.1], 2.36 q [SnCH(CH3)S, J 7.1], the pentyl proton
signals are the same as in the above spectrum. The
third fraction [1.81 g, bp 122 124 C (1.5 mm)] was
repeatedly distilled to obtain 1.75 g of the bis-sulfide
n-C5H11SCH2CH2SC5H11-n (VII), bp 148 149 C
Photoreaction of trimethylvinyltin with penta-
nethiol. A solution of 7.5 g of trimethylvinyltin,
6.15 g of 1-pentanethiol, and 0.075 g of benzoyl
peroxide in 50 ml of dry hexane was placed into a
quartz vessel and subjected to UV irradiation for 15 h
with stirring and cooling ( 50 to 70 C). The reaction
mixture was filtered at room temperature to separate
0.6 g of a solid substance not melting up to 280 C,
which could not be identified. The filtrate and excess
thiol were evaporated at reduced pressure (1.5 mm)
and room temperature. The residue was distilled in a
vacuum to obtain three fractions. The first fraction
(0.61 g; bp 68 70 C (1.5 mm)] was an inseparable
mixture of 1,1-bis(trimethylstannyl)ethane (V) and
1,2-bis(trimethylstannyl)ethane (VI). IR spectrum
1
(5 mm). H NMR spectrum (CDCl3), , ppm (J, Hz):
0.90 t (6H, CH3, J 7.0), 1.31 1.40 m [8H, S(CH2)2
(CH2)2CH3], 1.46 1.63 m (4H, SCH2CH2C3H7),
2.54 t (4H, SCH2C4H9, J 7.3), 2.72 s (4H, SCH2
CH2S). The unidentified still bottoms were 0.81 g.
S-(4-Methylphenyl)-S-[3-(trimethylstannyl)-
propyl]-N-(4-chlorophenylsulfonyl)sulfonimide
(VIII). A solution of 1.65 g of Chloramine-XB (98%
by active chlorine) in 20 ml of MeOH was added with
stirring to a solution of 1.95 g of sulfide II in 20 ml
of MeOH. The reaction mixture was heated under
reflux for 8 h, the NaCl residue was filtered off, the
filtrate was evaporated to dryness, the residue was
treated with 25 ml of CH2Cl2, and an additional NaCl
was filtered off. The overall yield of NaCl was 0.38 g
(100%). The filtrate was evaporated in a vacuum, and
the residue was extracted with ether in a Soxhlet
apparatus to obtain 2.85 g (93%) of sulfonimide VIII,
1
(thin film), , cm : 750 (SnMe), 520 (SnC).
(Me3Sn)2CHCH3 (V). 1H NMR spectrum (CDCl3),
,
ppm, (J, Hz): 0.05
s
[18H, 2(CH3)3Sn,
3
2J(H
/
117 119Sn) 49.2/51], 0.54 q (1H, SnCH, J 7.9),
1.43 d [3H, CCH3, 3J 7.9, J(H 117 119Sn) 73.9/77.3].
/
3
13C NMR spectrum (CDCl3), C, ppm (J, Hz): 9.83
[1J(C 117/119Sn) 297.8/311.6, 3J(C Sn) 8.2], 1.96
1
mp 111 112 C. IR spectrum, , cm : 1290 1260,
1070 [SO2 (as)], 1130 [SO2 (s)], 970 (SNIV), 925
1
(SNIV), 755 (SnMe); 520 (SnC). H NMR spectrum
[1J(C 117/119Sn) 292.5/305.9], 14.69 [2J(C Sn) 24.9].
Me3SnCH2CH2SnMe3 (VI). 1H NMR spectrum
(CDCl3), , ppm: 0.05 s [18 H, 2(CH3)3Sn], 0.99 s
(CDCl3), , ppm (J, Hz): 0.024 s (6H, Me3Sn), d
[Me3Sn, J(117Sn H) 51.4, J(119Sn H) 53.6], 0.677 and
0.750 m (2H, Sn CH2), 1.70 m (2H, CH2CH2CH2),
2.40 s (3H, C6H4CH3-4), 2.84 and 3.106 m (2H,
CH2S), 7.27 7.55 (AA BB system; 4H, C6H4Me-4),
7.29 7.79 (AA BB system; 4H, C6H4Cl-4). 13C NMR
spectrum (CDCl3), C, ppm (J, Hz): 10.4 (3C,
Me3Sn), d [Me3Sn, J(117Sn C) 317.0, J(119Sn C)
331.6], 8.8 (SnCH2), d [SnCH2, J(117Sn C) 312.8,
J(119Sn C) 326.8], 20.7 (CH2CH2CH2), 21.3 (C6H4C
H3), 57.6 (CH2S), 126.1 (o-CH, C6H4Me-4), 127.7 (o-
CH, C6H4Cl-4), 128.6 (m-CH, C6H4Cl-4), 130.5 (m-
CH, C6H4Me-4), 131.2 (p-CMe, C6H4Me-4), 137.1
(CSO2, C6H4Cl-4), 142.8 (p-CCl, C6H4Cl-4), 143.3
(CS=N, C6H4Me-4). Found, %: C 43.92; H 4.92;
S 12.05; Sn 22.75. C19H26ClNO2S2Sn. Calculated, %:
C 43.99; H 5.02; S 12.35; Sn 22.91.
(4H, 2CH2). 13C NMR spectrum (CDCl3), C, ppm (J,
Hz): 10.67 [1J(C 117/119Sn) 294.7/308.5, J(C Sn)
4
4.3], 6.84 [1J(C 117/119Sn) 339.2/355.6, 2J(C 117/119Sn)
1
36.0/37.6]. The H NMR spectra of these isomeric
compounds are consistent with those reported in
[10, 11]. The second fraction [7.7 g; bp 90 96 C
(1.5 mm)] was repeatedly distilled to obtain 6.3 g
(54%) of a mixture of silfides III and IV, bp 71 73 C
1
(0.5 mm). IR spectrum (thin film), , cm : 760
(SnMe), 525 (SnC). Me3SnCH2CH2SCH2CH2CH2
1
CH2CH3 (III). H NMR spectrum (CDCl3), , ppm (J,
Hz): 0.10
51.2/53.6], 0.87 0.92
s
[9H, (CH3)3Sn, 2J(H 117/119Sn)
m
(3H, C4H8CH3), 1.14
3
[AA XX system; SnCH2CH2S, JAX/AX 10.9/6.0],
1.28 1.41 m (4H, C2H4CH2CH23CH3), 1.60 1.72 m
(2H, CH2CH2C3H7), 2.67 t (2H, J 7.4, SCH2C4H9),
2.74 [AA XX system; 2H, SnCH2CH2S). 13C NMR
spectrum (CDCl3), C, ppm (J, Hz): 10.0 [(CH3)3Sn),
J(C 117/119Sn) 314.0/328.7], 11.4 [(SnCH2CH2S)
J(C 117/119Sn) 317.3/332.0], 13.9 (C4H8CH3), 22.3
(CH2CH2C3H7), 28.9 (C3HCH2CH3), 30.6 (C2H4CH2
4-Methylphenyl 3-(trimethylstannyl)propyl
sulfone (I). To a solution of 5.84 g of sulfide II in
100 ml of MeOH we added at 0 C dropwise with
stirring 3.62 g of 31% H2O2. The reaction mixture
was stirred for 3 h at 0 C and then for 6 h at room
temperature, after which it was evaporated in a
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 71 No. 7 2001

1044
SHCHERBAKOV et al.
vacuum at room temperature. The residue was treated
with 80 ml of warm hexane and filtered. The filtrate
was reduced to 20 ml and cooled to 10 C to isolate
5.07 g (79%) of sulfone I as colorless crystals, mp
CH2CH2CH2), 2.75 q (2H, C6H4CH2CH3, J 7.5),
3.07 m (2H, CH2SO2), 7.40 7.85 m (C6H4C2H5).
REFERENCES
1
53 54 C (from hexane). IR spectrum, , cm : 1270,
1080 [SO2 (as)], 1140 [SO2 (s)], 765 (SnMe), 520
(SnC). H NMR spectrum (CDCl3), , ppm (J, Hz):
1. Comprehensive Organic Chemistry, Barton, D. and
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371.
1
0.083 s (9H, Me3Sn), d [Me3Sn, J(H 117Sn) 51.2,
J(H 119Sn) 53.5], 0.81 m (2H, SnCH2), 1.92 m (2H,
CH2CH2CH2), 2.50 s (3H, C6H4CH3-4), 3.10 m (2H,
CH2SO2), 7.38 7.85 (AA BB system; 4H, C6H
4CH3-4). Found, %: C 43.58; H 6.28; S 8.77; Sn
32.20. C13H22O2SSn. Calculated, %: C 43.24; H 6.14;
S 8.88; Sn 32.38.
2. Belen’kii, L.I., Bzhezovskii, V.M., and Vlasova, N.N.,
Khimiya organicheskikh soedinenii sery. Obshchie
voprosy (Chemistry of Organic Sulfur Compounds.
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Khimiya, 1988, pp. 95 135.
Lithium salt IX. A 0.6 N solution of BuLi in
hexane (5.32 ml) was added with a syringe to a solu-
tion of 1.05 g of sulfone I in 15 ml of DMSO. A red-
brown precipitate of lithium salt IX formed. The re-
action mixture was shaken for 10 min and used in the
reaction with methyl iodide.
3. Al’fonsov, V.A., Belen’kii L.I., and Vlasova, N.N.,
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Reaction of lithium salt IX with methyl iodide.
Methyl iodide, 0.45 g, was added in a vacuum to the
suspension of lithium salt IX, obtained as described
above. The reaction mixture quickly decolorized. A
10% solution of NH4Cl (20 ml) was then added, the
organic layer was separated, the aqueous layer was
extracted with ether (3 50 ml), the combined organic
extracts were washed with water to neutral, dried with
Na2SO4, the solvent was removed, and the oily re-
sidue (1.00 g) was filtered on a glass filter and distil-
led in a vacuum to obtain 0.80 g (74%) of a mixture
of isomeric sulfides Xa and Xb as a viscous liquid,
5. Voronkov, M.G., Rakhlin, V.I., and Mirskov, R.G.,
Dokl. Akad. Nauk SSSR, 1973, vol. 209, no. 4,
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7. Shcherbakov, V.I., Stolyarova, N.E., and Kup-
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no. 2, pp. 371 374.
1
bp 188 189 C (1.5 mm). IR spectrum, , cm : 1290,
1080 [SO2 (as)], 1135 [SO2 (s)], 760 (SnMe), 525
(SnC). Me3SnCH2CH2CH(CH3)SO2C6H4CH3-4 (Xa).
1H NMR spectrum (CDCl3), , ppm: 0.053 s (9H,
CH3Sn), 0.53 1.00 m (2H, SnCH2), 1.27 d (3H,
CHCH3), 1.56 m and 2.17 m (2H, SnCH2CH2CH),
2.45 s (3H, C6H4CH ), 2.90 m (1H, CHSO2), 7.40
7.85 m (4H, C6H4CH33). Me3SnCH2CH2CH2SO2C6H4
8. Shcherbakov, V.I., Kuznetsova, V.P., Chuppu-
nov, E.V., Ovsetsina, T.I., Stolyarova, N.E., and Za-
kharov, L.N., Metalloorg. Khim., 1991, vol. 4, no. 6,
pp. 1350 1354.
9. Beilstein, vol. 6, H 425; E II 400.
10. Hosomi, A. and Traylor, T.G., J. Am. Chem. Soc.,
(CH2CH3)-4 (Xb). 1H NMR spectrum (CDCl3),
,
1975, vol. 97, no. 13, pp. 3682 3687.
ppm (J, Hz): 0.046 s (3H, CH3Sn), 0.80 m (2H,
SnCH2), 1.27 t (3H, C6H4CH2CH3), 1.89 m (2H,
11. Bulten, E.J. and Budding, H.A., J. Organomet. Chem.,
1976, vol. 111, no. 3, pp. C33 C34.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 71 No. 7 2001