58808-67-6Relevant academic research and scientific papers
Organylzinc Chalcogenolate Promoted Michael-Type Addition of α,β-Unsaturated Carbonyl Compounds
L?ren Nunes, Vanessa,De Oliveira, Ingryd Cristina,Soares Do Rêgo Barros, Olga
supporting information, p. 1525 - 1530 (2015/10/05)
We present the chemo-, regio-, and stereoselective synthesis of vinyl chalcogenide compounds promoted by organylzinc chalcogenolates. In this protocol, reductive cleavage of diorganyl dichalcogenide bonds by the Zn/NH4OH system led to organylzi
Activated Michael Acceptors as Precursors to Heterocycles. 1. 2-Azetidinones from 2-(Arylsulfonyl)propenoyl Chlorides and Amines
Zhou, Feng,Rosen, Jonathan,Zebrowski-Young, Jennifer M.,Freihammer, Patricia M.,Detty, Michael R.,Lachicotte, Rene J.
, p. 5403 - 5412 (2007/10/03)
The addition of NH3 and other primary amines to Z-3-phenyl-2-(arylsulfonyl)propenoyl chlorides gives trans-2-arylsulfonyl-3-phenyl-2-azetidinones as the major product in addition to the corresponding 2-arylsulfonyl-3-phenylpropenamide. Electron-withdrawing substituents in the arylsulfonyl group increased the percentage of products derived from 1,4-addition relative to 1,2-addition, while electron-donating substituents increased the amount of 1,2-addition observed in the product mixture. Addition of α-methylbenzylamine gave a 68:32 mixture of the two diastereomers of the trans-azetidinone. The major diastereomer was identified as the 1-(1R)-(3S,4S) and 1-(1S)-(3R,4R) enantiomers 16a by single-crystal X-ray crystallographic analysis. Phenylthio and phenylsulfoxo substituents did not promote 1,4-addition, although the addition of ammonia to Z-3-phenyl-2-(phenylsulfoxo)propenoyl chloride (7a) gave a 95:5 ratio of the corresponding propenamide 8a and a 3-(phenylsulfoxo)azetidinone 9a. trans-4-Phenyl-3-(arylsulfonyl)-2-azetidinones 12a and 12c were sulfonated by the pyridine-SO3 complex to give the corresponding N-sulfonates 28 in >80% yield. The p-methoxybenzyl substituent of 15 was removed by ceric ammonium nitrate in CH3CN to give 12a in 70% yield.
ADDITION OF THIOLS TO DERIVATIVES OF PHENYLPROPYNOIC ACID
Rasteikene, L. P.,Vidugirene, V. I.,Talaikite, Z. A.,Lukoshyavichyute, N. M.
, p. 647 - 651 (2007/10/02)
The reaction of thiophenol and benzyl hydrosulfide with phenylpropynoic acid, its methyl ester, and its anilide was investigated.The addition of thiophenol takes place regioselectively.Under the conditions of a radical reaction derivatives of 2-phenylthio
