Cis- and trans-2,4-dimethoxytetrahydropyran. Models for the study of the anomeric effect
- 1 May 1968
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 46 (9) , 1543-1548
- https://doi.org/10.1139/v68-253
Abstract
Acid-catalyzed methanolysis of 2-methoxy-5,6-dihydro-2H-pyran gave, in good yield, a 4.0:1.0 mixture of trans- and cis-2,4-dimethoxytetrahydropyran. Mild acid hydrolysis of 2-methoxy-5,6-dihydro-2H-pyran followed by acid-catalyzed reaction with methanol gave a cis-trans mixture of 4-hydroxy-2-methoxytetrahydropyran in very poor yield.From the equilibrium mixture of trans- and cis-2,4-dimethoxytetrahydropyran (4.0:1.0), the magnitude of the anomeric effect of the 2-methoxy group was calculated to be 1.4 kcal/mole.Keywords
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