Selective oxidation and chlorination of trifluoromethylsulfide using trichloroisocyanuric acid in ionic liquid

Halogenation of organic compounds in ionic liquids

“…66 Interestingly, the authors' original intention was chemoselective oxidation of aryl trifluoromethyl sulfides (39a,b) to the corresponding sulfoxides, but, instead, the chlorinated products (40a,b) were formed in high yield, even in excess TCICA (Scheme 19). A synthesis of 2,3-dichloropropionitrile was reported by the chlorination of acrylonitrile with molecular chlorine catalyzed by various ILs, namely imidazolium and pyridinium cations with Cl À , Br À , BF 4 À , and PF 6 À counterions.…”

One pot synthesis of trifluoromethyl aryl sulfoxides by trifluoromethylthiolation of arenes and subsequent oxidation with hydrogen peroxide

“…Triuoromethyl suldes are less reactive for oxidation and various oxidizing agents such as m-CPBA, CF 3 CO 3 H, NaIO 4 , TCCA, cyclic diacyl peroxide, Oxone, MoO 2 Cl 2 (OPPH 3 ) 2 /Cu(NO 3 ) 2 have been used and only two examples with H 2 O 2 (F 20 TPPFe and TFA) were reported (Scheme 1). 3,[18][19][20][21][22] As triuoromethyl suldes are less reactive, selectivity of oxidation is problematic and overoxidation to sulfones occurs readily. The problem with most oxidants is the formation of toxic waste and environmentally harmful by-products (metal salts, reagent residues).…”

A green and novel procedure for the preparation of ionic liquid

“…1-Alkyl-3-methylimidazolium hexafluorophosphate (AMImPF 6 ), 1-alkyl-3-methylimidazolium tetrafluoroborate (AMImBF 4 ), N-alkylpyridinium tetrafluoroborate (APyBF 4 ) and N-alkylpyridinium hexafluorophosphate (APyPF 6 ) are typically ionic liquids used as solvent or catalysts to extraction [4,5], polyborane reactions [6], hydroxylation of alkyl halides with water [7], syntheses of tribenzohexadehydro [12]annulene [8], fluorodediazoniation [9], regioselective nitration of aromatic compounds [10], oxidation [11], etc. There are two basic methods for the preparation of these ionic liquids: metathesis of a halide salt (Finkelstein step) with, for instance, a silver, group 1 metal or ammonium salt of the desired anion and acid-base neutralization reactions, but either way need the preparation of the imidazolium or pyridinium halides via alkylation (Menschutkin step) using a large molar excess of haloalkane (10-400%) for as long as 72 h at refluxing condition, and then RTILs was prepared with variable yields and much longer reaction time.…”