58911-63-0Relevant academic research and scientific papers
Evaluation of Chelation Effects Operative during Diastereoselective Addition of the Allylindium Reagent to 2- And 3-Hydroxycyclohexanones in Aqueous, Organic, and Mixed Solvent Systems
Paquette, Leo A.,Lobben, Paul C.
, p. 5604 - 5616 (2007/10/03)
The unprotected 2- and 3-hydroxycyclohexanones 1-8 were prepared by methods that skirted as much as possible their proclivity for α-ketol rearrangement (where the possibility for such isomerization exists). The diastereofacial selectivity of their reactio
Axial/equatorial proportions for 2-substituted cyclohexanones
Basso,Kaiser,Rittner,Lambert
, p. 7865 - 7869 (2007/10/02)
Axial-equatorial conformational proportions have been measured for 2- substituted cyclohexanones in chloroform by the Eliel method for F, Cl, Br, I, MeO, MeS, Me2N, MeSe, and Me. For the first seven of these, at least five experimentally independent measurables were used and the resulting conformational preferences appear to be accurate to within 10%. Systematic errors degraded the results for MeSe and Me. For Me2N, the conformational preference also was measured for the first time at slow exchange in the low- temperature 13C spectrum in several solvents. In chloroform, steric and polar effects contribute to the conformational preferences, with steric effects dominant for large groups such as I and MeS.
