Cleavage of the phenacyl esters of carboxylic and thiocarboxylic acids by metal alkoxides

Journal Article · Sun Nov 20 04:00:00 UTC 1988 · J. Org. Chem. USSR (Engl. Transl.); (United States)

OSTI ID:5950442

Morozov, A A

During the cleavage of phenacyl esters with general formula XC/sub 6/H/sub 4/COCH/sub 2/OCOR by metal alkoxides in alcohols and in ether-alcohol solutions the acids, esters, and ethers are formed as a result of cleavage of the C-C bond. The solvent participates in the formation of the ether and gives rise to transesterification of RCOOCH/sub 3/ with catalytic participation of the metal alkoxide. The reactivity of the phenacyl esters of the thio acids is much higher. Before dissociation the esters of substituted benzoins C/sub 6/H/sub 5/COCH(OCOCH/sub 3/) /times/ C/sub 6/H/sub 4/X-4 undergo irreversible rearrangement with the formation of isomeric products.

• Research Organization: Institute of Organic Chemistry, Frunze (USSR)
• OSTI ID: 5950442
• Journal Information: J. Org. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Org. Chem. USSR (Engl. Transl.); (United States) Vol. 24:6; ISSN JOCYA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
ACTIVATION ENERGY
ALCOHOLS
ALKALI METAL COMPOUNDS
ALKALINE EARTH METAL COMPOUNDS
ALKOXIDES
CARBOXYLIC ACID ESTERS
CATALYSIS
CATALYTIC EFFECTS
CHEMICAL REACTION KINETICS
CHEMICAL REACTIONS
CHROMATOGRAPHY
DISSOCIATION
ENERGY
ESTERIFICATION
ESTERS
HYDROXY COMPOUNDS
INFRARED SPECTRA
ISOMERIZATION
KINETICS
METHANOL
ORGANIC COMPOUNDS
ORGANIC SULFUR COMPOUNDS
REACTION KINETICS
SEPARATION PROCESSES
SODIUM COMPOUNDS
SPECTRA
STEREOCHEMISTRY