Synthesis of 4-methyl-2,3,4-trichlorotetrahydropyran and several features of the stereochemistry of the nucleophilic substitution of the. cap alpha. -chlorine atom

Journal Article · Wed Oct 01 00:00:00 EDT 1986 · Chem. Heterocycl. Compd. (Engl. Transl.); (United States)

DOI:https://doi.org/10.1007/BF00542774· OSTI ID:6181677

Gevorkyan, A A; Arakelyan, A S; Dvoryanchikov, A I

A convenient method has been developed for the synthesis of 4-methyl-2,3,4-trichlorotetrahydropyran by the chlorination of 4-methyl-4-chlorotetrahydropyran, 4-methyl-5,6-dihydro-2H-pyran and its dichloride. A study was carried out on the reactions of 4-methyl-2,3,4-trichlorotetrahydropyran with alcohols, with sodium thiocyanate and grignard reagents. PMR spectroscopy was used to study the stereochemistry of 4-methyl-2,3,4-trichlorotetrahydropyran and its derivatives, 2-substituted 4-methyl-3,4-dichlorotetrahydropyrans. The dechlorination of these dichloro derivatives by metallic sodium leads to 2,4-disubstituted 5,6-dihydro-2H-pyrans with high regioselectivity.

• Research Organization: Institute of Organic Chemistry, Erevan, USSR
• OSTI ID: 6181677
• Journal Information: Chem. Heterocycl. Compd. (Engl. Transl.); (United States), Vol. 22:4; Other Information: Translated from Khim. Geterotsikl. Soedin.; 22: No.4, 465-471(Apr 1986)
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC
ORGANIC
PHYSICAL AND ANALYTICAL CHEMISTRY
74 ATOMIC AND MOLECULAR PHYSICS
PYRANS
CHLORINATION
STEREOCHEMISTRY
STRUCTURAL CHEMICAL ANALYSIS
SYNTHESIS
ALCOHOLS
CHEMICAL SHIFT
CHLOROFORM
CHROMATOGRAPHY
COUPLING CONSTANTS
DEUTERIUM COMPOUNDS
DOUBLE RESONANCE METHODS
GRIGNARD REAGENTS
ISOMERIZATION
ISOMERS
J-J COUPLING
MAGNETIC DIPOLE MOMENTS
MOLECULAR STRUCTURE
NMR SPECTRA
SODIUM COMPOUNDS
TETRAHYDROPYRAN
THIOCYANATES
ALKALI METAL COMPOUNDS
ALKALINE EARTH METAL COMPOUNDS
ANTITHYROID DRUGS
CARBONIC ACID DERIVATIVES
CHEMICAL REACTIONS
CHLORINATED ALIPHATIC HYDROCARBONS
COUPLING
DIPOLE MOMENTS
DRUGS
HALOGENATED ALIPHATIC HYDROCARBONS
HALOGENATION
HETEROCYCLIC COMPOUNDS
HORMONE ANTAGONISTS
HYDROGEN COMPOUNDS
HYDROXY COMPOUNDS
INTERMEDIATE COUPLING
MAGNESIUM COMPOUNDS
MAGNETIC MOMENTS
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
ORGANIC SULFUR COMPOUNDS
ORGANOMETALLIC COMPOUNDS
SEPARATION PROCESSES
SPECTRA
400201* - Chemical & Physicochemical Properties
640302 - Atomic
Molecular & Chemical Physics- Atomic & Molecular Properties & Theory