Aqueous High-Temperature Chemistry of Carbo- and
Heterocycles. 28. Reactions of Aryl Sulfoxides and
Sulfones in Sub- and Supercritical Water at 200−460 °C
Alan R. Katritzky
Richard A. Barcock
Elena S. Ignatchenko
Steven M. Allin
Michael Siskin
Carl W. Hudson
10.1021/ef960073x.s001
https://acs.figshare.com/articles/journal_contribution/Aqueous_High-Temperature_Chemistry_of_Carbo-_and_Heterocycles_28_Reactions_of_Aryl_Sulfoxides_and_Sulfones_in_Sub-_and_Supercritical_Water_at_200_460_C/3595971
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.
1997-01-21 00:00:00
formic acid
Sulfoxide
sulfoxide
methyl phenyl sulfones
sodium formate