A Novel Route for the Synthesis of Unsaturated Oxo Sulfones and Bissulfones

Abstract

The reaction between vinyl chloride and aroyl/arylsulfonyl chloride under FriedelÐCraftÕs reaction conditions was the basis for the synthesis of unsaturated oxo sulfones and bissulfones.

N-heterocyclic carbene-catalyzed rearrangements of vinyl sulfones

“…13 Trans -1,2-bis(arylsulfonyl)ethylene has been used in organic synthesis, 14 but its preparation typically involves the use of vinyl chloride gas. 15 Alternatively, the straightforward preparation of 1,1-bis(phenylsulfonyl)ethylene involves paraformaldehyde, piperidine, and acid. 12 b …”

Facile Polyethylene Glycol (PEG-400) Promoted Synthesis of Some New Heteryl (E)-styryl Sulfones

“…All the reagents and solvents were pure, purchased from commercial otherwise stated. 3-(2-Bromoacetyl)coumarins, [23][24] styrene-sulfonylchlorides 25 and sodium (E 26 were prepared by literature procedure. Melting points were determined in open capillaries with a " Cintex " melting point apparatus Mumbai, India and were uncorrected.…”

Synthesis and Reactions of 2-Chlorovinyl Sulfones

“…Some methods of synthesis of 2-chlorovinyl sulfones from different sulfones or sulfonyl chlorides were presented. Thus, treatment of 2,2-dichloroethanesulfonylarenes with Et 3 N [18,19], Et 3 N / PhH [20][21][22] or Et 3 N / CH 2 Cl 2 [23] selectively leads to formation only of E-isomers of 2-chlorovinyl sulfones. For example, reaction of 2,2-dichloroethanesulfonylbenzene (10) with Et 3 N in mixture of diethyl ether and dichloromethane at 15 o C afforded product (E)-5 in 97% yield [24].…”

“…Reaction of 2chlorovinyl sulfones 31 with Na 2 S in dioxane [37] or MeOH [38] afforded sulfides 32 in yields up to 90%. Sulfinic acids and 2-chlorovinyl sulfones in the presence of NaHCO 3 [32] or salts of sulfinic acids in MeOH [20] also gave the corresponding addition products. Phenylselenol was successfully added to 2chlorovinyl sulfones in the presence of Et 3 N / PhH [39], Et 3 N/ PhMe [34] and Cs 2 CO 3 / 18-crown-6 / PhMe [34].…”