2-ALKOXY-3-HYDROXYTETRAHYDROPYRANS AND 2-ALKOXY-3-HYDROXYTETRAHYDROFURANS: I. PREPARATION, STRUCTURE, AND SOME DERIVATIVES
Open Access
- 1 July 1966
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 44 (13) , 1571-1576
- https://doi.org/10.1139/v66-234
Abstract
Oxidation of 2,3-dihydrofuran or 2,3-dihydropyran with peroxybenzoic acid or m-chloroperoxybenzoic acid in the presence of an alcohol has produced, respectively, trans-2-alkoxy-3-hydroxytetrahydrofurans in 59 to 64% yield and trans-2-alkoxy-3-hydroxytetrahydropyrans in 65 to 80% yield. In the presence of acids, these acetals isomerize readily to give an equilibrated mixture of cis and trans isomers.Keywords
This publication has 7 references indexed in Scilit:
- Methyl 2,6-Anhydro-3,4-di-O-methyl-α-D-mannoside. An Intramolecular Nucleophilic Displacement of Mesylate with InversionThe Journal of Organic Chemistry, 1965
- Reductions with Metal Hydrides. XIV. Reduction of 2-Tetrahydropyranyl and 2-Tetrahydrofuranyl EthersThe Journal of Organic Chemistry, 1965
- THE INFLUENCE OF SUBSTITUENTS ON THE EASE AND DIRECTION OF RING OPENING IN THE LiAlH4–AlCl3 REDUCTIVE CLEAVAGE OF SUBSTITUTED 1,3-DIOXOLANESCanadian Journal of Chemistry, 1964
- Reactions of Hydrogen Peroxide. VII. Alkali-Catalyzed Epoxidation and Oxidation Using a Nitrile as Co-reactantThe Journal of Organic Chemistry, 1961
- Mechanisms Of Epoxide ReactionsChemical Reviews, 1959
- Configurational Effects on the Proton Magnetic Resonance Spectra of Six-membered Ring Compounds1Journal of the American Chemical Society, 1958
- 1-O-Benzoyl-α-D-talopyranoseJournal of the American Chemical Society, 1957