1195-93-3Relevant articles and documents
N,N′-Dichlorobis(2,4,6-trichlorophenyl)urea (CC-2): An efficient reagent for conversion of oximes to ketones
Gupta, Arvind K.,Acharya, Jyotiranjan,Pardasani, Deepak,Dubey, Devendra K.
, p. 411 - 414 (2008/02/12)
A method for the rapid conversion of oximes into the corresponding carbonyl compounds using N,N′-dichlorobis (2,4,6-trichlorophenyl)urea (CC-2) at room temperature is described. The method is economical as the solid by-product bis(2,4,6-trichlorophenyl)urea could be removed by filtration and recycled after re-chlorination.
Ozonolyses of 1-alkyl-substituted 1-tert-butylethylenes and highly methylated methylenecycloalkanes. The influence of the substituent steric bulk on the direction of cleavage of the primary ozonides
Kawamura, Shin-Ichi,Yamakoshi, Hideyuki,Abe, Manabu,Masuyama, Araki,Nojima, Masatomo
, p. 891 - 896 (2007/10/03)
Ozonolyses of 1-alkyl-substituted 1-tert-butylethylenes and of highly methylated methylenecycloalkanes were conducted in the presence of trifluoroacetophenone (7) in ether. The ozonolysis of 2,2,6-trimethyl-1-methylenecyclohexane provided only the crossed-ozonide 10 derived from capture of formaldehyde O-oxide with the ketone 7 in 42% yield, while in the case of the relevant 2,2,5-trimethyl-1-methylenecyclopentane the alternative crossed-ozonide 15e derived from cycloaddition of 2,2,5-trimethylcyclopentanone O-oxide with the ketone 7 was the sole isolable product. The total energies of two possible cycloreversion processes for the primary ozonide 12c and for 12e, calculated at B3LYP/6-31G**//B3LYP/3-21G* level of theory, seem to reproduce the observed difference in the regiochemistry of fragmentation between these two primary ozonides.
Oxidation of α-Substituted Cyclohexanols by Nitric Acid
Smith, John R. Lindsay,Thomas, C. Barry,Whittaker, Mark
, p. 2191 - 2194 (2007/10/02)
The influence of α-substituents on the oxidative cleavage of cyclohexanol by nitric acid in the presence of copper(II) and vanadium(V) ions has been investigated.Following the initial oxidation to give the cyclohexanone, further reaction, leading to ring opening of the ketone, requires at least one α-hydrogen.Thus 2,2,6,6-tetramethylcyclohexanol is converted to the corresponding ketone whilst 2,2,6-trimethylcyclohexanol is oxidised to a mixture of dicarboxylic acids.The mechanisms of the oxidations are discussed and enolisation is shown to be the key to oxidative cleavage.For ketones that can give two alternative enols, reaction occurs predominantly via the more stable tautomer.