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), Journal Name: Chem. Heterocycl. Compd. (Engl. Transl.); (United States) Vol. 22:4; ISSN CHCCA
• Country of Publication: United States
• Language: English

Related Subjects

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