Characterization of Epoxides of cis- and trans-4-(p-Chlorophenyl)-5-cyanocyclohexene from NMR Spectra of Derivatives

Autor:	Alain C. Huitric, David Roll
Rok vydání:	1966
Předmět:	Chromatography Gas Magnetic Resonance Spectroscopy Stereochemistry Chemistry Chemistry Pharmaceutical Pharmaceutical Science Ether Benzoates NMR spectra database chemistry.chemical_compound Cyclohexanes Ethers Cyclic Diethyl ether Cis–trans isomerism
Zdroj:	Journal of Pharmaceutical Sciences. 55:942-947
ISSN:	0022-3549
DOI:	10.1002/jps.2600550914
Popis:	The epoxidation of cis -4-( p -chlorophenyl)-5-cyanocyclohexene with m -chloroper-benzoic acid in diethyl ether yielded trans -4-( p -chlorophenyl)- trans -5-cyano-1, 2-epoxycyclohexane as the only product. Epoxidation of trans -4-( p -chlorophenyl)-5-cyanocyclohexene with m -chloroperbenzoic acid yielded cis -4-( p -chlorophenyl)- trans -5-cyano-1,2-epoxycyclohexane and trans -4-( p -chlorophenyl)- cis -5-cyano-1,2-epoxy-cyclohexane in ratio of about 7 to 3, respectively, when carried out in ether but in ratio of about 1 to 1 in 1,2-dichloroethane. The epoxides were characterized from the NMR spectra of the derived diols, mono-, and diacetates by taking advantage of the difference between the spatial 1,3-diaxial deshielding effects of hydroxyl and acetoxy groups.
Databáze:	OpenAIRE
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