Experimental and Theoretical Evidence of Through-Space Electrostatic Stabilization of the Incipient Oxocarbenium Ion by an Axially Oriented Electronegative Substituent During Glycopyranoside Acetolysis
- 1 October 1997
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 62 (22), 7597-7604
- https://doi.org/10.1021/jo970677d
Abstract
No abstract availableKeywords
This publication has 15 references indexed in Scilit:
- 1994 R.U. Lemieux Award Lecture Hydrolysis of acetals and ketals. Position of transition states along the reaction coordinates, and stereoelectronic effectsCanadian Journal of Chemistry, 1994
- General atomic and molecular electronic structure systemJournal of Computational Chemistry, 1993
- Cyclization of Hydroxyenol Ethers into Spiroacetals. Evidence for the position of the transition state and its implication on the stereoelectronic effects in acetal formationHelvetica Chimica Acta, 1992
- An ab initio study (6-31G*) of transition states in glycoside hydrolysis based on axial and equatorial 2-methoxytetrahydropyransJournal of the American Chemical Society, 1991
- Concerning the antiperiplanar lone pair hypothesis: oxidative hydrolysis of conformationally restrained 4-pentenyl glycosidesJournal of the American Chemical Society, 1989
- Complete kinetic isotope effect description of transition states for acid-catalyzed hydrolyses of methyl .alpha.- and .beta.-glucopyranosidesJournal of the American Chemical Society, 1986
- Solvent Polarity and the Anomeric EffectAngewandte Chemie-International Edition, 1986
- Acetolysis of permethylated O-alkyl glycopyranosides: kinetics and mechanismThe Journal of Organic Chemistry, 1983
- Trapping of the oxocarbonium ion intermediate in the hydrolysis of acetophenone dimethyl ketalsJournal of the American Chemical Society, 1977
- 572. Monoalkyl hexoses: improved procedures for the preparation of 1- and 3-methyl ethers of fructose, and of 3-alkyl ethers of glucoseJournal of the Chemical Society, 1951