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Synthesis of Sulfonyl Chlorides and Sulfonic Acids
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sulfate was filtered off and the organic phase was concentrated un-
der reduced pressure to give the pure product.
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An identical procedure was employed using 30% H2O2 (2 mmol, 0.2
mL) and POCl3 (1 mmol, 0.153 g) in the presence SDS (1 CMC, 5
mL) for the oxidative chlorination of disulfides (Table 1). The spec-
tral and physical properties of known products were compared to
those reported in the literature. In every case excellent agreement
was obtained.
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Synthesis of Sulfonic Acids; General Procedure
To a micellar solution of SDS (1 CMC, 5 mL) in H2O, thiol (1
mmol) and 30% H2O2 (5 mmol, 0.5 mL), were added. POCl3 (1
mmol, 0.153 g) was added and the mixture was stirred at 80 °C until
the starting material was consumed (see Table 2). The progress of
the reaction was monitored by TLC. At the end of the reaction, ex-
cess H2O2 was deactivated by the addition of saturated aqueous
Na2S2O3. Subsequently, KCl was added to the reaction mixture, and
the resulting precipitate of dodecyl sulfate was filtered off. After re-
moval of water under vacuum on a rotary evaporator, the organic
material was extracted with ethanol. The solvent was removed un-
der reduced pressure to give spectroscopically pure product. When
necessary, the crude product was recrystallized (EtOAc–n-hexane).
A similar procedure was applied using 30% H2O2 (4 mmol, 0.4 mL)
and POCl3 (1 mmol, 0.153 g) in the presence of SDS (1 CMC, 5
mL) for the synthesis of a range of sulfonic acids from the corre-
sponding disulfide derivatives (Table 2).
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All the products are known compounds and were easily identified
by comparison of their spectroscopic data with those reported. The
1H and 13C NMR spectra for the sulfonic acids and some sulfonyl
chlorides are available as Supporting Information. Accurate melting
points were often difficult to determine because of the hygroscopic
nature of sulfonic acids.
Supporting Information for this article is available online at
Acknowledgment
We are thankful to the Razi University Research Council for partial
support of this work.
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