453-18-9Relevant articles and documents
Analyse structurale des derives fonctionnels des acides carboxyliques. Partie II. Halogeno et cyanoacetates de methyle
Maury, Catherine,Petrissans, Jean
, p. 267 - 278 (1991)
Methylene bending mode analysis and dipole moment determinations were carried out in solution (CCl4) for some methyl esters ΣCH2CO2Me with Σ =F(I), Cl(II), Br(III), I(IV), CN(V), in order to identify the conformers induced by ΣCH2 group rotating motion and determine their relation amounts.The results are consistent with the existence of two conformations; syn and anti for (I), syn and gauche for (II) and (III).Compounds (IV) and (V) occur almost exclusively in gauche and syn forms respectively.A theoretical study of compounds (I), (II) and (V) by P.C.I.L.O. methods and the Onsager formalism was performed.The collected data show that the conformers have the O-Me bond syn to the carbonyl.The calculated value of ΔE for the equilibrium between the syn and anti rotamers (Ea-Es =600 cal mol-1) is in good agreement with ΔH0298 estimated from the temperature-dependence studies (ΔE =158 cal mol-1).
Novel and practical preparation of α-fluoro-functionalized esters from fluoroiodoacetates
Zhi, Chengxin,Chen, Qing-Yun
, p. 1741 - 1747 (2007/10/03)
The addition reaction of fluoroiodoacetates 2 to various electron-rich alkenes 3 initiated by iron powder in dry THF at 70-80°C gave 1:1 adducts 4 in good yields. A variety of functionalities in the alkenes such as trimethylsilyl, alkoxy, acetoxy, hydroxy and ester could be tolerated under the reaction conditions. Reduction of the adducts 4 with Zn-AcOH in ethanol or Zn-NiCl2·OH2O in moist THF was readily accomplished, and the overall procedure was amenable to a convenient one-flask procedure. Treatment of fluoroiodoacetates 2 with electron-deficient alkenes 7 in the presence of an Fe-CrCl3·OH2O-bpy bimetal redox system in ethanol at 70-80°C resulted in the formation of iodine-free 1:1 adducts 8 in moderate to good yields. It is proposed that the addition reactions of fluoroiodoacetates 2 to electronrich and electron-deficient alkenes proceeded through a single-electron-transfer mechanism.