J Org Chem
Chemistry Department, University College London, Gower Street, London WC1E 6BT, UK.
Published: April 2005
[reaction: see text] A study of published crystal structures (of O-acetylated sugars for the most part) suggests that the exocyclic C-O bond in acetate esters of cyclic alcohols intrinsically prefers a staggered conformation, although the eclipsed conformation is only slightly less stable. When the acetate is flanked by two equatorial substituents the preferred conformation is close to eclipsed. Over 1500 C-OAc bonds have been analyzed. Diagnostic NMR criteria for torsion angles and MM3 calculations are reported and confirm these conclusions.
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http://dx.doi.org/10.1021/jo048295c | DOI Listing |
Int J Biol Macromol
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Department of Chemistry, The Scripps Research Institute, La Jolla, CA, USA.
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