87406-33-5Relevant articles and documents
Regiospecific ring opening of some methyl- and phenyl-substituted 1,1,2-trihalocyclopropanes to acetylenic acetals or ketals by variation of reaction conditions
Bakstad, Einar,Sydnes, Leiv K.
, p. 1029 - 1033 (2007/10/03)
Regiospecific ring opening of six title compounds has been achieved under various reaction conditions. With dry sodium ethoxide in dry THF as reagent acetylenic diethyl ketals are obtained in 66-81% isolated yield. With DBU in dry ethanol, the corresponding acetylenic diethyl acetals are formed and isolated in 50-67% yield. Finally, treatment of the substrates with 50% aqueous sodium hydroxide in the presence of 2-propanol, triethylbenzylammonium chloride and dichloromethane gave acetylenic diisopropyl acetals, in 82% yield at the best. By-product formation was negligible in most cases. Acta Chemica Scandinavica 1998.
A Route from 1,1,1,3-Tetrachloro-3-phenylpropane to Ethynyl Phenyl Ketone Involving Elimination of Hydrogen Chloride and 1,3-Proton Transfer
Akiyama, Takeo,Yoshida, Yasuki,Hanawa, Tokiko,Sugimori, Akira
, p. 1795 - 1798 (2007/10/02)
The treatment of 1,1,1,3-tetrachloro-3-phenylpropane with alkali in ethanol affords ethynyl phenyl ketone and its acetal in good yields.This reaction proceeds through the elimination of hydrogen chloride and an efficient 1,3-proton transfer catalyzed by base.Ethyl cinnamate is obtained in only 2percent yield.
