Graphite/methanesulfonic acid (GMA) as a new reagent for sulfonylation of phenols and thia-Fries rearrangement of aryl sulfonates to sulfonylphenols
A new facile method for direct sulfonylation of phenols was developed. Graphite in methanesulfonic acid (GMA) was used to prepare sulfonylphenols by sulfonylation of phenol and naphthalene derivatives with p-toluenesulfonic acid (=4-methylbenzenesulfonic acid) (Table 1) and the thia-Fries rearrangement of aryl sulfonates (Table 4). Mechanistic studies showed that the sulfonylation reaction of phenols in GMA occurred through an initial sulfonate formation followed by a thia-Fries rearrangement of the aryl sulfonate by an intermolecular mechanism (Scheme 3).
Al2O3/MeSO3H (AMA) as a new reagent for the thia-Fries rearrangement of arylsulfonates to hydroxyaryl sulfones
A new facile method for thia-Fries rearrangement of arylsulfonates has been developed. A variety of arylsulfonates rearrange in excellent yields in the presence of Al2O3/MeSO3H as a new reagent without the use of any solve
Sharghi, Hashem,Shahsavari-Fard, Zahra
p. 2491 - 2501
(2007/10/03)
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