Journal of Molecular Structure p. 300 - 309 (2019)
Update date:2022-07-30
Topics:
Tittal, Ram Kumar
Ram, Ram Nath
Nirwan, Ayushi
Ghule, Vikas D.
Kumar, Satish
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.
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Doi:10.1016/S0040-4020(97)00871-5
(1997)Doi:10.1016/S0022-1139(00)81929-6
(1986)Doi:10.1055/s-2002-32971
(2002)Doi:10.1039/f19827801923
(1982)Doi:10.1016/0039-128X(64)90024-8
(1964)Doi:10.1039/b607504e
(2006)