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Cyclohexene derivatives, such as imines, epoxides, and halonium ions, react with nucleophiles in a stereoselective fashion, affording trans-diaxial addition products. The term “Trans-diaxial addition” describes the mechanism of the addition, however the products are likely to equilibrate by ring flip to the lower energy conformer, placing the new substituents in the equatorial position.
Examples of absolute configuration of some carbohydrates and amino acids according to Fischer projection (D/L system) and Cahn–Ingold–Prelog priority rules (R/S system) The R/S system is an important nomenclature system for denoting enantiomers. This approach labels each chiral center R or S according to a system by which its substituents ...
Base-induced bimolecular dehydrohalogenation (an E2 type reaction mechanism). The optimum geometry for the transition state requires the breaking bonds to be antiperiplanar, as they are in the appropriate staggered conformation. The mechanism requires that the departing atoms or groups follow antiparallel trajectories.
Cyclohexane is the most stable of the cycloalkanes, due to the stability of adapting to its chair conformer. [4] This conformer stability allows cyclohexane to be used as a standard in lab analyses. More specifically, cyclohexane is used as a standard for pharmaceutical reference in solvent analysis of pharmaceutical compounds and raw materials.
Cyclohexane chair flip (ring inversion) reaction via boat conformation [8] The interconversion of equivalent chair conformers of cyclohexane (and many other cyclic compounds) is called ring flipping. Carbon–hydrogen bonds that are axial in one configuration become equatorial in the other, and vice versa.
Because the hydrogen abstraction is radical, any chiral configuration at the δ-carbon racemizes. [14] The reaction also has a quite large hydrogen isotope effect: in the decomposition of 10, the ratio of 1,2-dimethylpyrrolidine 11 and 1,2-dimethylpyrrolidine-2-d 12 (determined by combustion and IR spectra) suggests k H ⁄ k D ≈ 3.42–3.54.
English: Cyclohexane chair flip (ring inversion) reaction. Structures of the significant conformations (A, B, C & D) of the reaction are shown & plotted against their ...
It is the prototypical example of a pericyclic reaction with a concerted mechanism. More specifically, it is classified as a thermally allowed [4+2] cycloaddition with Woodward–Hoffmann symbol [π 4 s + π 2 s]. It was first described by Otto Diels and Kurt Alder in 1928.