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The reaction proceeds through the formation of a chromate ester (1) from nucleophilic attack of the chlorochromate by the allylic alcohol. The ester then undergoes a [3,3]-sigmatropic shift to create the isomeric chromate ester (2). Finally, oxidation of this intermediate yields the α,β-unsaturated aldehyde or ketone product (3). [1]
1,4-Cyclohexadiene is an organic compound with the formula C 6 H 8. It is a colourless, flammable liquid that is of academic interest as a prototype of a large class of related compounds called terpenoids, an example being γ-terpinene. An isomer of this compound is 1,3-cyclohexadiene.
A copper chromite catalyst is usually used industrially. [1] The cis/trans ratio of the CHDM is affected by the catalyst. [2] Byproduct of this process are 4-methylcyclohexanemethanol (CH 3 C 6 H 10 CH 2 OH) and the monoester methyl 4-methyl-4-cyclohexanecarboxylate (CH 3 C 6 H 10 CO 2 CH 3, CAS registry number 51181-40-9). [3]
[4] [5] [6] These reactions are metal-catalyzed and proceed through a metallacyclobutane intermediate. [7] It was first published by Dider Villemin in 1980 describing the synthesis of an Exaltolide precursor, [ 8 ] and later become popularized by Robert H. Grubbs and Richard R. Schrock , who shared the Nobel Prize in Chemistry , along with Yves ...
[1] The general chemical formula of the halogen addition reaction is: C=C + X 2 → X−C−C−X (X represents the halogens bromine or chlorine, and in this case, a solvent could be CH 2 Cl 2 or CCl 4). The product is a vicinal dihalide. This type of reaction is a halogenation and an electrophilic addition.
The silver salt 1 reacts with bromine to form the acyl hypohalite intermediate 2. Formation of the diradical pair 3 allows for radical decarboxylation to form the diradical pair 4, which recombines to form the organic halide 5. The trend in the yield of the resulting halide is primary > secondary > tertiary. [2] [3]
Cyclohexanol is produced by the oxidation of cyclohexane in air, typically using cobalt catalysts: [5]. 2 C 6 H 12 + O 2 → 2 C 6 H 11 OH. This process coforms cyclohexanone, and this mixture ("KA oil" for ketone-alcohol oil) is the main feedstock for the production of adipic acid.
Compared with its isomer cyclohexa-1,4-diene, cyclohexa-1,3-diene is about 1.6 kJ/mol more stable. [5] Cyclohexadiene and its derivatives form (diene)iron tricarbonyl complexes. Illustrative is [(C 6 H 8)Fe(CO) 3], an orange liquid. This complex reacts with hydride-abstracting reagents to give the cyclohexadienyl derivative [(C 6 H 7)Fe(CO) 3 ...