Efficient preparation of E-β-iodovinyl phenylsulfone by Finkelstein reaction at a vinylic center

Synthesis and investigation on liquid crystal and optical properties of dyads based on triphenylene and perylene

“…10,14 The intermediates u-iodo-alkoxy-triphenylenes (compounds 6-9) were obtained by reacting compounds 2-5 with excessive potassium iodide in acetone under reuxing according to Finkelstein reaction. 20 The raw u-iodo-alkoxy-triphenylene products without further purication were then reacted with perylene monoanhydride diesters in the presence of 1-hexanol and anhydrous potassium carbonate at 50 C to give the target dyads. Since the perylene monoanhydride diesters were not soluble well in these reactions, as well as the reaction solutions were highly viscous, it took about 72 hours to obtain the dyads in the yields of 28-40% for the last two steps.…”

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].…”

“…Chlorine atom in 2-chlorovinyl sulfones was readily substituted by iodine atom [23] or hydroxyl group. Thus, treatment of compound (E)-5 with an excess of NaI in acetone at 130 o C afforded thr corresponding iodo derivative 18 in 76% yield.…”

The synthesis of thiols, selenols, sulfides, selenides, sulfoxides, selenoxides, sulfones and selenones

“…328 (E)-β-Iodovinyl phenyl sulfone has been prepared in good yield from 1,2,2-trichloroethane via a sequence of reactions including a stereospecific addition-elimination step which converts (E)-β-chlorovinyl phenyl sulfone into the corresponding iodide. 329 The addition of trifluoromethanesulfonyl chloride to acyclic and cyclic vinyl ethers gives the corresponding β-alkoxy vinyl trifluoromethyl sulfones in good yield (Scheme 176). 330 A chiral pool approach to enantiomerically pure γ-hydroxy and γ-amino vinyl sulfones has been reported.…”