137540-83-1Relevant academic research and scientific papers
Crystal structures of β-chalcogeno-α, β-unsaturated chalcogenoesters: Novel intramolecular interaction between the carbonyl oxygen and the chalcogen atom at the β-position
Ozaki, Toshiya,Nomoto, Akihiro,Ogawa, Akiya
experimental part, p. 579 - 585 (2012/01/19)
A series of β-chalcogeno-α, β-unsaturated chalcogenoesters (1 and 2) were synthesized, and their molecular structures were investigated in detail by X-ray crystal analyses. Interestingly, intramolecular interactions between the carbonyl oxygen and the chalcogen atom at the β-position (β-S ...O and β-Se...O) were observed in most cases, and intermolecular π-π interaction and hydrogen bonding were observed in the case of δ-hydroxy derivatives (1b and 2b).
Palladium-catalyzed addition and carbonylative addition of diaryl disulfides and diselenides to terminal acetylenes
Kuniyasu, Hitoshi,Ogawa, Akiya,Miyazaki, Shin-Ichiro,Ryu, Ilhyong,Kambe, Nobuaki,Sonoda, Noboru
, p. 9796 - 9803 (2007/10/02)
Novel transition-metal-catalyzed reactions of disulfides and diselenides with acetylenes are described. In the presence of tetrakis(triphenylphosphine)palladium(0), [Pd(PPh3)4], the (1) of diaryl disulfides and diselenides to terminal acetylenes 1 takes place stereoselectively to give high yields of (Z)-1,2-bis(arylthio)-1-alkenes 2 and (Z)-1,2-bis(arylseleno)-1-alkenes 3 respectively A mechanistic proposal includes the following: (1) oxidative addition of (ArY)2 [Y = S, Se] to low-valent palladium species, (2) stereoselective cis-thiopalladation or cis-selenopalladation to acetylenes to form a cis-vinylpalladium intermediate and (3) reductive elimination of the product with retention of the stereochemistry. When the reaction of diaryl disulfides and diselenides with terminal acetylenes is performed under the pressure of carbon monoxide, the carbonylative addition occurs to afford (Z)-1,3-bis(arylthio)-2-alken-1-ones 4 and (Z)-1,3-bis(arylseleno)-2-alken-1-ones 5, respectively. Carbon monoxide is regioselectively incorporated on the side of the terminal carbon of the acetylenes.
