Reaction with Carboxylic Acids and their Derivatives

Reaction with Carboxylic Acids and their Derivatives 

With trichloroacetic acid and trifluoroacetic acid epoxyfatty acid esters are converted to dihydroxy esters. The opening of alkyl- and aryloxiranes with aryl carboxylates has been investigated in the presence of tertiary amine (Eqs. 311 and 312).  

Equation 311 shows a possible reaction pathway of the process. 

The opening of cyclohexene oxide with monochloroacetic acid is not a selective reaction bis(Zra/is-2-hydroxycyclohexyl)ether mono(chloroacetates) and trans-2-(chloroacetoxy)cyclohexanol are formed. In an aprotic solvent with benzoic acid, indene oxide gives only trans product. The reaction of oxirane with monochloroacetic acid esters is shown in Eq. 313.  

Monoesters of diastereomeric 1,2-diols can be prepared from oxiranes with camphanic acid. The acetolysis of epoxycyclopentanes and further transformations of the unexpected product of acetolysis (Eq. 314) have been followed in acidic and basic media. 

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E. Reaction with Carboxylic Acids and their Derivatives... 

Oxiranes yield oxazolines with nitriles in the presence of strong acids. The reaction proceeds with inversion, with complete stereospecificity. A new application of the Ritter reaction has been reported the opening of epimeric steroid-16,17-oxiranes in acidic medium with acetonitrile. The reactions of unsaturated hydroxynitriles formed from a-ethylenic oxiranes have been investigated. Numerous publications have appeared on the kinetics of reactions with carboxylic acids and their derivatives. ° ... 

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