Water → HCID 10219472, compound

HRID 1978210Notes

Reaction equation

HRID 1978210 reaction equation
[CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.[N+]([O-])([O-])=O.[NH4+].[Ce].[OH2:13].[C:14](#[N:16])[CH3:15]>>[C:14]([NH:16][CH:1]1[CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1)(=[O:13])[CH3:15]

Participants

5

Reactant 4

HCID 962WaterHCID 6342AcetonitrileHCID 8079CyclohexeneHCID 57418452Ammonium cerium-nitrate

Product 1

HCID 10219472HCID 10219472, compound

Procedure

Briguet, C. Freppel, J.-C. Richer and M. Zador (Can. J. Chem. 1974, 52, 3201) describe a process for the oxidation of cyclohexene with cerium ammonium nitrate in acetonitrile which contains 1% of water, and they obtain acetamido-2-cyclohexene. Here, the use of stoichiometric amounts of cerium ammonium nitrate stands in the way of industrial use. Y. Leblanc, R. Zamboni, M. A. Bernstein (J. Org. Chem. 1991, 56, 1971) describe an ene reaction of cyclohexene with bis-(2,2,2-trichloroethyl) azodicarboxylate at 155° C. which, after work-up, affords a yield of 70% of the desired tetrahydroaniline derivative.

Sources & evidence

ORD record
ord-b5ad40be6c1e45f2a6f28b4871c6208b
Source dataset
uspto-grants-2001_05
Patent number
US06235925B1

Reaction notes

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