77355-29-4Relevant academic research and scientific papers
One-pot approach for the regioselective synthesis of β-keto sulfones based on acid-catalyzed reaction of sulfonyl chlorides with arylacetylenes and water
Lai, Chunbo,Xi, Chanjuan,Jiang, Yanfeng,Hua, Ruimao
, p. 513 - 515 (2007/10/03)
Reaction of sulfonyl chlorides with arylacetylenes and water in the presence of a catalytic amount of sulfonic acid in THF provided β-keto sulfones in good yields with excellent regioselectivity.
Reactions of (Aryloxy)oxosulfonium Ylides with Carbonyl Compounds
Okuma, Kentaro,Nakanishi, Kazuto,Ohta, Hiroshi
, p. 1402 - 1407 (2007/10/02)
Reactions of (aryloxy)oxosulfonium salts with alkyllithium followed by the additon of carbonyl compounds gave β-aryloxy sulfones, β-aroyloxy sulfones, and α,β-unsaturated or β,γ-unsaturated sulfones in 1.4-17.9percent, 1.2-7.2percent, and 4.5-13.5percent yields, respectively.Ylides obtained by treatment of these sulfonium salts with n-BuLi reacted with carbonyl compounds to give betaines, which formed unusual four-membered cyclic alkoxyoxosulfonium salts.The aryloxy anions thus formed attacked β-carbons of these salts to afford β-aryloxy sulfones.The aroyloxy anion that might be formed by autoxidation also attacked β-carbons of these salts to afford β-aroyloxy sulfones.When these anions attacked the α- or γ-protones of these salts, unsaturated sulfones were obtained.This is the first example that the reaction of ylide with carbonyl compounds gave sulfone derivatives via four-membered cyclic alkoxyoxosulfonium salts that were produced by the intramolecular SN2 mechanism.The yields of unsaturated sulfones were raised up to 35-60percent by a one-pot reaction.
