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The Wohl–Ziegler reaction [1] [2] is a chemical reaction that involves the allylic or benzylic bromination of hydrocarbons using an N-bromosuccinimide and a radical initiator. [3] Best yields are achieved with N-bromosuccinimide in carbon tetrachloride solvent. Several reviews have been published. [4] [5]
The NBS product precipitates and can be collected by filtration. [2] Crude NBS gives better yield in the Wohl–Ziegler reaction. In other cases, impure NBS (slightly yellow in color) may give unreliable results. It can be purified by recrystallization from 90 to 95 °C water (10 g of NBS for 100 mL of water). [1]
The trans-cycloheptene isomerization mechanism is not simple alkene-bond rotation, but rather an alternative lower energy pathway. [2] Based on the experimentally observed second order reaction kinetics for isomerization, two trans -cycloheptene molecules in the proposed pathway first form a diradical dimer .
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.
Benzene is converted to cyclohexylbenzene by acid-catalyzed alkylation with cyclohexene. [6] Cyclohexylbenzene is a precursor to both phenol and cyclohexanone. [7] Hydration of cyclohexene gives cyclohexanol, which can be dehydrogenated to give cyclohexanone, a precursor to caprolactam. [8] The oxidative cleavage of cyclohexene gives adipic acid.
Reactions of conjugated double-bond systems can be synthesized into cycloalkenes through electrocyclic reactions. [13] Addition of heat or photolysis causes a reversible reaction that causes one pi bond to become a sigma bond, which closes the ring and creates a cycloalkene. [11] Formation of a cycloalkane via an electrocyclic reaction
Cyclohexa-1,3-diene is an organic compound with the formula (C 2 H 4)(CH) 4. It is a colorless, flammable liquid. It is a colorless, flammable liquid. Its refractive index is 1.475 (20 °C, D).
The epoxidation can take place either in a homogeneous reaction by peracids [2] or heterogeneous catalysis (e.g. silver and molecular oxygen). [ 3 ] [ 4 ] [ 5 ] In industrial production the heterogeneously catalyzed synthesis is preferred because of better atom economy , a simpler separation of the product and easier recycling of catalyst.