Reaction of dichlorocarbene with 2-phenyl-1,3-oxathiolane

Journal Article · Tue Oct 20 04:00:00 EDT 1987 · J. Org. Chem. USSR (Engl. Transl.); (United States)

OSTI ID:6974870

Nazarov, D V; Safiev, O G; Zorin, V V; Rakhmankulov, D L

It was established that the reaction of 2-phenyl-1,3-oxathiolane (I) with dichlorocarbene, generated from chloroform in 50% aqueous solution of sodium hydroxide with the use of triethylbenzylammonium chloride as phase-transfer catalyst, leads to the formation of dichloromethyl thiobenzoate (II) and ethylene with yields of 24 and 38% respectively and 60% conversion in the substrate (I). The reaction was conducted at 35-40/sup 0/C for 24 h with the following amounts of the reagents; 0.5 mole of the substrate (I); 5 moles of chloroform; 600 mol of 50% aqueous sodium hydroxide solution; 1 g of triethylbenzylammonium chloride. Compound (II) was isolated by column liquid chromatography on aluminum oxide (40-250 ..mu..) with a 1:5 mixture of diethyl ether and hexane as eluant. The product was identified by means of the IR, PMR, and /sup 13/C NMR spectra.

• Research Organization: Ufa Petroleum Institute (USSR)
• OSTI ID: 6974870
• Journal Information: J. Org. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Org. Chem. USSR (Engl. Transl.); (United States) Vol. 23:5; ISSN JOCYA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
ACTIVATION ENERGY
ALKANES
ALKENES
AMINES
AMMONIUM CHLORIDES
AMMONIUM COMPOUNDS
AMMONIUM HALIDES
BENZOIC ACID
CARBENES
CARBON 13
CARBON ISOTOPES
CARBOXYLIC ACID ESTERS
CARBOXYLIC ACIDS
CATALYSIS
CATALYTIC EFFECTS
CHEMICAL REACTIONS
CHEMICAL SHIFT
CHLORIDES
CHLORINATED ALIPHATIC HYDROCARBONS
CHLORINATION
CHLORINE COMPOUNDS
CHLOROFORM
CHROMATOGRAPHY
CYCLOALKANES
DEUTERIUM COMPOUNDS
ENERGY
ESTERS
ETHYLENE
EVEN-ODD NUCLEI
HALIDES
HALOGEN COMPOUNDS
HALOGENATED ALIPHATIC HYDROCARBONS
HALOGENATION
HYDROCARBONS
HYDROGEN COMPOUNDS
INFRARED SPECTRA
ISOTOPES
LIGHT NUCLEI
MONOCARBOXYLIC ACIDS
NMR SPECTRA
NUCLEI
ORGANIC ACIDS
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC SULFUR COMPOUNDS
QUATERNARY COMPOUNDS
RADICALS
SEPARATION PROCESSES
SPECTRA
STABLE ISOTOPES
SYNTHESIS