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Paper Information

Journal:   JOURNAL OF THE IRANIAN CHEMICAL SOCIETY(JICS)   AUGUST 2012 , Volume 9 , Number 4; Page(s) 507 To 512.
 
Paper: 

SULFONYLATION OF AROMATIC COMPOUNDS WITH METHYL P-TOLUENESULFONATE AS A SULFONYLATING PRECURSOR

 
 
Author(s):  KHODAEI M.M.*, NAZARI E.
 
* DEPARTMENT OF CHEMISTRY AND NANO SCIENCE AND NANOTECHNOLOGY RESEARCH CENTER (NNRC), RAZI UNIVERSITY, 67149 KERMANSHAH, IRAN
 
Abstract: 

We have developed Friedel-Crafts (FC) sulfonylation of aromatic compounds with methyl p-toluenesulfonate as a sulfonylating precursor. In this procedure, methyl p-toluenesulfonate was treated and activated with pyridine to produce N-methylpyridinium p-toluenesulfonate as a sulfonylation reagent. Reactivity of this salt for the sulfonylation of mesitylene was investigated in the presence of three different promoters, such as triflic anhydride, dimethylsulfide ditriflate, and triphenylphosphine ditriftate (TPPD). All of the promoters show chemoselectivity and among them, TPPD presents a chemoselectivity in FC sulfonylation.

 
Keyword(s): SULFONYLATION, ARENES, METHYL P-TOLUENESULFONATE, TRIPHENYLPHOSPHINE DITRIFLATE, SULFONES
 
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