10.1016/S0040-4039(00)87344-X
The study aimed to elucidate the mechanism of the condensation of enol dichloroacetylene with trichloroethylene to form α-dichlorovinyl ketone, which was previously unclear. The study concluded that the reaction proceeds via dichloroacetylene as an essential intermediate and the mechanism is elimination-addition. The fate of the initial adduct of dichloroacetylene and enol depends on the competition between unimolecular elimination of Cl- and bimolecular proton abstraction. The key chemicals used in the process include trichloroethylene, dichloroacetylene (ClC≡CCl), lithium diisopropylamide (LDA), hexamethylphosphoramide (HMPA) and lithium bis(trimethylsilyl)amide (LiN(SiMe3)2). The study also involved the use of deuterated trichloroethylene to study the isotope effect, supporting the proposed mechanism. This work has important implications for the synthetic scope of haloacetylene chemistry in the ethynylation and vinylation of enol systems.
10.1007/BF00899356
The study focuses on the synthesis of multiply substituted ethanes. The key chemicals involved include trichloroethylene, sodium phenolate, and phenol. Trichloroethylene reacts with sodium phenolate to form dichlorovinyl-phenyl ether (I), which then undergoes a complex sequence of reactions with phenol to produce tetra-(p-oxyphenyl)-ethane (IV). The study also explores the hydriding of dichlorovinyl-phenyl ether (I) using catalysts like palladium on carbon, platinum oxide, and Raney nickel, resulting in the formation of phenetol (III). Additionally, the study synthesizes derivatives of tetra-(p-oxyphenyl)-ethane (IV), such as tetra-(p-methoxyphenyl)-ethane (V), tetra-(p-ethoxyphenyl)-ethane (VI), tetra-(p-acetoxyphenyl)-ethane (VII), and tetra-(3-nitro-4-oxyphenyl)-ethane (VIII), through methylation, acetylation, and nitration processes. The study investigates the structure and properties of these compounds, including their potential estrogenic activity, which was tested but found to be inactive up to 100 gamma.
T:Toxic;
