143675-91-6Relevant articles and documents
Synthesis and NMR spectroscopic conformational analysis of benzoic acid esters of mono- and 1,4-dihydroxycyclohexane, 4-hydroxycyclohexanone and the -ene analogue – The more polar the molecule the more stable the axial conformer
Kleinpeter, Erich,Werner, Peter,Linker, Torsten
, p. 3801 - 3809 (2017/06/13)
para-Substituted benzoic acid esters of cyclohexanol, 1,4-dihydroxycyclohexane, 4-hydroxy-cyclohexanone and of the corresponding exo-methylene derivative were synthesized and the conformational equilibria of the cyclohexane skeleton studied by low temperature 1H and 13C NMR spectroscopy. The geometry optimized structures of the axial/equatorial chair conformers were computed at the DFT level of theory. Only one preferred conformation of the ester group was obtained for both the axial and the equatorial conformer, respectively. The content of the axial conformer increases with growing polarity of the 6-membered ring moiety; hereby, in addition, the effect of sp2 hybridization/polarity of C(4)=O/C(4)=CH2 on the present conformational equilibria is critically evaluated. Another dynamic process could be studied, for the first time in this kind of compounds.
Oxidative conversion of aldoximes into carboxylic acid esters
Said,Skarzewski,Mlochowski
, p. 1851 - 1862 (2007/10/02)
Aromatic and aliphatic aldoximes or their O-methyl ethers can be efficiently converted into the corresponding carboxylic acid esters by treatment with an alcoholic solution of 30% hydrogen peroxide in the presence of catalytic amounts of 2-nitrobenzeneseleninic acid. Primary alcohols give excellent to good yields, secondary ones - good to moderate, but with tertiary alcohols no esterification is observed.