Effect of the nature and position of substituents in the aromatic ring on catalytic rearrangement of 1,3-bis(2-chlorophenoxy) and 1,3-bis(4-chlorophenoxy)-2-methylenepropanes

Journal Article · Thu Oct 20 00:00:00 EDT 1988 · J. Org. Chem. USSR (Engl. Transl.); (United States)

OSTI ID:5887698

Krasnov, V A; Levashova, V I; Bunina-Krivorukova, L I

Unlike the thermal rearrangement, the catalytic rearrangement of 1,3-bis(2-chlorophenoxy)- and 1,3-bis(4-chlorophenoxy)-2-methylenepropanes takes place by an intermolecular mechanism with the participation of only one O-C bond and subsequent cyclization of the obtained ether phenols to coumarans; the rearrangement is faster in the case of the 2-chloro-substituted ether. The subsequent participation of the two O-C bonds in the isomerization is observed in the case of 1,3-bis(2,4-dichlorophenoxy)-2-methylenepropane on account of the retarded cyclization.

• Research Organization: Lensovet Leningrad Technological Institute (USSR)
• OSTI ID: 5887698
• Journal Information: J. Org. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Org. Chem. USSR (Engl. Transl.); (United States) Vol. 24:5; ISSN JOCYA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
ALCOHOLS
AROMATICS
BORON COMPOUNDS
BORON FLUORIDES
CATALYSIS
CATALYTIC EFFECTS
CHEMICAL REACTION KINETICS
CHEMICAL REACTIONS
DEHYDROCYCLIZATION
ETHERS
FLUORIDES
FLUORINE COMPOUNDS
GLYCOLS
HALIDES
HALOGEN COMPOUNDS
HYDROXY COMPOUNDS
INFRARED SPECTRA
ISOMERIZATION
KINETICS
MASS SPECTRA
NMR SPECTRA
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
PHENOLS
REACTION KINETICS
SPECTRA
STRUCTURAL CHEMICAL ANALYSIS