Aqueous High-Temperature Chemistry of Carbo- and Heterocycles. 28. Reactions of Aryl Sulfoxides and Sulfones in Sub- and Supercritical Water at 200−460 °C
1997-01-21T00:00:00Z (GMT)
by
Diphenyl and methyl phenyl sulfones and sulfoxides and dibenzothiophene
sulfone were treated
at 460 °C with water, 15% aqueous formic acid, and 15% aqueous
sodium formate. Thermal
comparisons were run in cyclohexane, and for those compounds and
conditions that resulted in
fast conversion after 7 min at 460 °C, also at lower temperatures.
Sulfoxides are highly reactive,
sulfones less so. Reactivity is greatest in 15% aqueous sodium
formate followed by formic acid
for the sulfones; this reactivity order is inverted for the sulfoxides.
In all of the aqueous media,
ionic reactions dominate. The sulfoxides are mainly deoxygenated
to the corresponding sulfides,
while C−S bond cleavage is more important for the sulfones.
Product slates are identified and
analyzed, and reaction pathways are suggested for the transformations
found.
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