123630-49-9Relevant academic research and scientific papers
Selective Synthesis of Tetrasubstituted Olefins by Copper-Mediated Acetoxythiolation of Internal Alkynes: Scope and Mechanistic Studies
Villuendas, Pedro,Ruiz, Sara,Vidossich, Pietro,Lledós, Agustí,Urriolabeitia, Esteban P.
supporting information, p. 13124 - 13135 (2018/09/11)
The Cu-mediated synthesis of tetrasubstituted olefins by the addition of an acetate group and a thiolate to an unactivated internal alkyne is described. The reaction is fully stereoselective, because only the E alkene is obtained. If the alkyne is asymmetric, the reaction also shows a very high degree of regioselectivity. The mechanism of the reaction is elucidated by DFT methods, which show that it takes place through Cu-stabilized radical species. Calculations highlight the crucial role of the dimeric copper(II) diacetate in the process, as it generates the active species in which the sulfur center has an incipient thiyl radical character and accepting, through a series of changes in the oxidation states of the two copper centers, the two electrons released in the addition of two nucleophiles to the alkyne.
Electrophilic Addition of 4'-Nitrobenzenesulphenanilide to Alkynes in Acetic Acid. A Synthesis of β-Acetoxyvinyl Sulphides
Benati, Luisa,Casarini, Daniele,Montevecchi, Pier Carlo,Spagnolo, Piero
, p. 1113 - 1116 (2007/10/02)
4'-Nitrobenzenesulphenanilide reacts at room temperature with simple alkyl- and aryl-alkynes in acetic acid in the presence of boron trifluoride-diethyl ether to afford products of acetoxysulphenylation in moderate to good yields.The addition products are
