Chemistry of Heterocyclic Compounds p. 380 - 386 (1986)
Update date:2022-09-26
Topics:
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-trichlorotetrachloropyran 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
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