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In 1937, Marc Tiffeneau, Weill, and Tchoubar published in Comptes Rendus their finding that 1-aminomethylcycloahexanol converts readily to cycloheptanone upon treatment with nitrous acid. [4] Perhaps due to such a large ring being expanded, the authors did not immediately relate it to the Demjanov rearrangement.
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.
Cyclohexenone is also used in multi-step synthesis in the construction of polycyclic natural products. It is prochiral. With strong bases, the positions 4 and 6 (the two CH 2-groups of the carbonyl group and the C-C double bond adjacent) are deprotonated. Cyclohexenone is an in-vitro catalyst for a relatively mild decarboxylation of alpha amino ...
It then appears that the reaction proceeds mainly by a trans mechanism and, following the Zaitsev rule, 1-methylcyclohexene is preferentially formed in the early stages of the reaction. Indeed, if only about 10% of the total distillate is collected as the first fraction, one finds that the alkene is about 93% l-methylcyclohexene: at the end of ...
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] The leading producers in CHDM are Eastman Chemical in US and SK Chemicals in ...
1,2-Diaminocyclohexane (DACH) is an organic compound with the formula (CH 2) 4 (CHNH 2) 2. It is a mixture of three stereoisomers: cis-1,2-diaminocyclohexane and both enantiomers of trans-1,2-diaminocyclohexane. The mixture is a colorless, corrosive liquid, although older samples can appear yellow. It is often called DCH-99 and also DACH.
In the total synthesis of (−)-heptemerone B and (−)-guanacastepene E, attached with trans-2-phenylcyclohexanol, the glyoxylate reacted with 2,4-dimethyl-pent-2-ene, in the presence of tin(IV) chloride, yielding the desired anti adduct as the major product, together with a small amount of its syn isomer with 10:1 diastereomeric ratio. [17]
The enantioselective synthesis was accomplished by J. K. Whitesell by adding Pseudomonas fluorescens lipase to racemic trans-2-phenylcyclohexyl chloroacetate. [1] [2] This enzyme is able to hydrolyze the ester bond of the (−)-enantiomer but not the (+)-enantiomer.