REPLACEMENT REACTIONS IN THE QUINIC ACID SERIES
- 1 October 1963
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 41 (10) , 2417-2423
- https://doi.org/10.1139/v63-356
Abstract
The action on D-quinic acid of hot 95% acetic acid containing mineral acid gave, after complete acetylation, 1,4,5-tri-O-acetyl-epi-quinide consisting of approximately equal portions of the (−)- and (±)-isomers, and tetra-O-acetyl-scyllo-quinic acid. The stereochemistry of the products and their derived free polyols were determined by nuclear magnetic resonance (n.m.r.) spectroscopy and synthesis.Elimination of the tosyloxy group in 5-tosyl-epi-quinicol was shown to take place readily in aqueous acetic acid with participation of the primary carbinol group to give an anhydro quinicol derivative and epi-quinicol.Keywords
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