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

Journal Article · Sun Nov 20 00:00:00 EST 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), Vol. 24:6; Other Information: Translated from Zh. Org. Khim.; 24: No. 6 1264-1270 (Jun 1988)
• Country of Publication: United States
• Language: English

Related Subjects

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