Thermodynamics of vinyl ethers—XV : Halogen-containing vinyl ethers |
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Authors: | E Taskinen E Sainio |
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Institution: | Department of Chemistry, University of Torku, 20500 Turku 50, Finland |
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Abstract: | Thermodynamics of geometrical and prototropic isomerization reactions on some halogen-containing vinyl ethers of the types ROCH–CHX (X = Cl, Br), ROC(CH2X)CH2 (X = F, Cl, Br), and ROC(CHMeCl)CH2 (R = Me, Et, Et2CH) have been studied. In ROCHαCHβX the cis (or Z) isomer is thermodynamically the more stable isomer, the higher stability of the Z isomer being due to its lower enthalpy. The relative stability of the E and Z forms is, however, reversed if the α H atom is replaced by a Me group. In systems like OCCX the double-bond stabilizing ability of the halogen atom decreases in the order Cl > Br > F, in contrast to the case in haloalkenes, where the corresponding order is F > Cl > Br. |
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