91077-70-2Relevant academic research and scientific papers
Regio- and Stereoselective Hydrosulfonation of Alkynylcarbonyl Compounds with Sulfinic Acid in Water
Wu, Chao,Yang, Panpan,Fu, Zhimin,Peng, Yong,Wang, Xin,Zhang, Zuozhi,Liu, Fang,Li, Wenyi,Li, Zhizhang,He, Weimin
, p. 10664 - 10671 (2016/11/29)
We report the atom-economic and environmentally friendly synthesis of Z-β-sulfonyl-a,β-unsaturated carbonyl compounds in water. The mechanism study reveals that the hydrosulfonylation of alkynylcarbonyl compounds with sulfinic acids proceeds via a mechanism that features a sulfinic acid molecule protonating an alkynyl motif to form the ethenium intermediate, which subsequently reacted with a sulfonyl anion to afford the desired products. The ethenium intermediate differentiated electronic and steric demands between the two substituents on the C≡C triple bond of the alkyne substrates to exhibit high regio- and stereoselectivity from a wide range of Z-β-sulfonyl-a,β-unsaturated carbonyl compounds.
Arylsulfonylpyrroles from reaction of tosylmethyl isocyanide (tosmic) with 3-arylsulfonyl acrylates as michael acceptors
Di Santo, Roberto,Costi, Roberta,Massa, Silvio,Artico, Marino
, p. 1801 - 1815 (2007/10/03)
Ethyl 3-(arylthio)acrylates did not react with α-alkali metalated tosylmethyl isocyanide (TosMIC) to afford 4-(arylthio)pyrrole-3-carboxylic acid ethyl esters. Oxidation of thioethers to sulfones generated reactive 3- (arylsulfonyl) acrylates, which promptly underwent cycloaddition with TosMIC in the presence of base giving ethyl 4-(arylsulfonyl)pyrrole-3-carboxylates. Contrary to expectation, the use of ethyl 3-(5-chloro-2- nitrophenylsulfonyl)acrylate led to ethyl ester of 5-tosylpyrrole-3- carboxylic acid instead of the expected ethyl 4-(5-chloro-2- nitrophenylsulfonyl)pyrrole-3-carboxylate.
