Synthesis of dichloroketene acetals under conditions of phase-transfer catalysis and their reactions with sulfur-containing electrophiles

Journal Article · Sun Jul 10 04:00:00 EDT 1988 · J. Org. Chem. USSR (Engl. Transl.); (United States)

OSTI ID:5971271

Guseva, S A; Mirskova, A N; Levkovskaya, G G; Kalikhman, I D; Voronkov, M G

A method was developed for the production of dichloroketene acetals by the dehydrochlorination of chloral acetals in DMFA in the presence of triethylbenzylammonium chloride as phase-transfer catalyst. Sulfur monochloride, sulfur dichloride, and benzene sulfenyl chloride react with dichloroketene acetals with the formation of adducts (alkoxycarbonyldichloromethanesulfenyl chloride ClSCCl/sub 2/ COOR, alkoxycarbonyldichloromethanethiosulfenyl chloride ClSSCCl/sub 2/COOR, and butyl phenylthiodichloroacetate C/sub 6/H/sub 5/SCCl/sub 2/COOR respectively). The action of secondary amines on butoxycarbonyldichloromethanesulfenyl chloride gave sulfenamides R/sup 1/R/sup 2/NSCCl/sub 2/COOBu. The reactions of butoxycarbonyldichloromethanethiosulfenyl chloride and butyl phenylthiodichloroacetate with secondary amines under various conditions led to degradation products.

• Research Organization: Irkutsk Institute of Organic Chemistry (USSR)
• OSTI ID: 5971271
• Journal Information: J. Org. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Org. Chem. USSR (Engl. Transl.); (United States) Vol. 24:2; ISSN JOCYA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
ACETALS
ADDUCTS
ALDEHYDES
ALKALI METAL COMPOUNDS
AMIDES
AMINES
AMMONIUM CHLORIDES
AMMONIUM COMPOUNDS
AMMONIUM HALIDES
CATALYSIS
CATALYTIC EFFECTS
CHEMICAL REACTION YIELD
CHEMICAL REACTIONS
CHLORAL
CHLORIDES
CHLORINATED ALIPHATIC HYDROCARBONS
CHLORINE COMPOUNDS
CHLOROFORM
CHROMATOGRAPHY
DECHLORINATION
DEHALOGENATION
DEHYDROGENATION
DEUTERIUM COMPOUNDS
ETHERS
HALIDES
HALOGEN COMPOUNDS
HALOGENATED ALIPHATIC HYDROCARBONS
HETEROGENEOUS CATALYSIS
HYDROGEN COMPOUNDS
HYDROXIDES
INFRARED SPECTRA
KETENES
NMR SPECTRA
OPTIMIZATION
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
ORGANIC SULFUR COMPOUNDS
OXYGEN COMPOUNDS
POTASSIUM COMPOUNDS
POTASSIUM HYDROXIDES
QUATERNARY COMPOUNDS
SEPARATION PROCESSES
SPECTRA
SULFUR CHLORIDES
SULFUR COMPOUNDS
SYNTHESIS
YIELDS