Related Experiment Video
Updated: Aug 18, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
threo-2-(2,6-dimethoxyphenoxy)-1-(4-hydroxy-3,5-dimethoxyphenyl)propane-1,3-diol: a conformational study
Knut Lundquist1, Shiming Li, Vratislav Langer
1Department of Forest Products and Chemical Engineering, Chalmers University of Technology, SE-41296 Göteborg, Sweden.
Abstract:
In the crystal structure of the title compound, C19H24O8, the molecules adopt a conformation in which the bulky 2,6-dimethoxyphenoxy and 4-hydroxy-3,5-dimethoxyphenyl groups are almost as far apart as possible. The C(aryl)...C(aryl) distance is 4.8766 (19) A, which is close to the calculated maximum value (4.92 A). The C(aryl)-C-C-O(aryloxy) torsion angle is 173.76 (11) degrees and the C(benzylic)-C-O-C(aryl) torsion angle is 149.09 (11) degrees. The conformation is compared with those of related lignin model compounds. The hydrogen-bonding pattern is discussed in terms of graph-set theory.
Related Concept Videos
Structure and Nomenclature of Alcohols and Phenols
Alcohols are one of the most important functional groups in organic chemistry. The name of alcohol comes from the hydrocarbon from which it is derived. Alcohols are organic molecules containing the functional hydroxyl or –OH group directly bonded to carbon. Phenols have an OH group directly attached to a benzene ring. While alcohols are colorless, phenol is a white crystalline compound with a characteristic "hospital smell" odor.
As with other organic compounds, alcohols and phenols...
Preparation of Diols and Pinacol Rearrangement
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids
Prochirality
Stereoisomerism of Cyclic Compounds
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

