239798-31-3Relevant academic research and scientific papers
CuCl/bpy-promoted unusual Z-stereoselective synthesis of trichloroacetic acid phenyl ester for Hirshfeld surface analysis and DFT study
Tittal, Ram Kumar,Ram, Ram Nath,Nirwan, Ayushi,Ghule, Vikas D.,Kumar, Satish
, p. 300 - 309 (2019)
A trichloromethyl ester devoid of suitably substituted C[dbnd]C bond, any leaving group or a H-atom at the β-position to the radical, which are otherwise known for ATRA/ATRC, 1,2-rearrangement/fragmentation or simple 1,2-H shift respectively, in a reaction of trichloro-acetic acid phenyl ester with 2 mol equiv CuCl/bpy in reflux DCE or benzene under inert N2 condition resulted to stereoselective synthesis of Z-2,3-dichloro-but-2-enedioic acid diphenyl ester and/or formation of reductive de-chlorination side product. The Z-stereochemistry of the product was confirmed by X-ray diffraction spectroscopy of Z-2,3-dichloro-but-2-enedioic acid dinaphthalen-1-yl ester which crystalizes in monoclinic system of P21/c symmetry elements. Hirshfeld surface analysis of experimentally established structure of Z-2,3-dichloro-but-2-enedioic acid diphenyl ester unrevealed the intermolecular interactions showing both H-bonding and short contacts. The stereochemistry was also interpreted computationally using Density Functional Theory at B3LYP/6-311G(d,p) level of theory. The calculated energies, energy gap and balance between the electrostatic potential on the molecular surface were computed which revealed unusual formation of less stable Z-isomer.
A novel synthesis of 2-trichloromethylchromones and 7-trichloromethylnorkhellin
Sosnovskikh, Vyacheslav Ya.,Usachev, Boris I.
, p. 1007 - 1009 (2007/10/03)
The reaction of 2-hydroxyacetophenones with trichloroacetyl chloride in the presence of pyridine at -30°C followed by treatment of the reaction mixture with potassium tert-butylate affords 2-hydroxy-2-trichloromethylchroman-4-ones. Dehydration then provides the 2-trichloromethyl-chromones.
