Conformational Studies of D-Glycals by ¹H Nuclear Magnetic Resonance Spectroscopy
Abstract
The Preferred Half-Chair Conformations of the Fully O-Acetylated D-Glycals (And Related Compounds), as Indicated by 1H N.m.r. Spectroscopy Show that the Coupling Constant 4J2,4 is the Most Sensitive to Conformational Change. All Six Fully O-Acetylated-D-Glycals Favour the 4H5(D) Conformation in Solution, Except Di-O-Acetyl-D-Xylal Which Adopts the Alternative 5H4(D) Conformation. These Conformational Preferences Can Be Rationalised by Considering the Interactions between the Substituants at C(3), C(4), and C(5) and the ' Allylic Effect '. with the Introduction of a Substituent at C(2) in Glucals and Galactals, Ring-Flattening or Inversion to the 5H 4 Conformation Can Take Place to Relieve Strain.
Recommended Citation
Chalmers, A. A., & Hall, R. H. (1974). Conformational Studies of D-Glycals by ¹H Nuclear Magnetic Resonance Spectroscopy. Journal of the Chemical Society, Perkin Transactions 2(6), pp. 728-732. Royal Society of Chemistry.
The definitive version is available at https://doi.org/10.1039/P29740000728
Department(s)
Business and Information Technology
International Standard Serial Number (ISSN)
1472-779X
Document Type
Article - Journal
Document Version
Citation
File Type
text
Language(s)
English
Rights
© 2023 Royal Society of Chemistry, All rights reserved.
Publication Date
01 Jan 1974
