Journal article
Structural studies on sulfonylbicyclo[n.2.0]alkan-1-ols
Journal of Physical Organic Chemistry, Vol.15(11), pp.733-741
2002
Abstract
The structures of a series of sulfonylbicyclo[n.2.0]alkan‐1‐ols (n = 3–6) 1–6 were determined by single‐crystal x‐ray diffraction. A survey of the Cambridge Structural Database and Monte Carlo conformational searches using MacroModel were performed. Compounds 1, 3 and 4 show intramolecular hydrogen bonding. Compound 2 is stabilized by three‐centered ‘bifurcated’ intra‐ and intermolecular hydrogen bonds between the hydroxyl proton and the sulfone oxygens. Compounds 5 and 6 are stabilized by intermolecular hydrogen bonds formed between the trans 1‐hydroxy and sulfonyl moieties. In compounds 1–6, the degree of cyclotorsion of the four‐ five‐, six‐, seven‐ and eight‐membered rings adjacent to the bond between the bridgehead atoms C1 and C4 is reflected in the magnitude about the exterior angles about C1 (C2—C1—Cx) and C4 (C3—C4—C5). The six‐membered ring systems of 2, 5 and 6 showed noteworthy increases in the C5—C4—C1—Cx and C3—C4—C1—C2 torsion angles, and this was attributed to the conformational constraints of the pseudo‐chair conformation of the six‐membered ring. Similar conformational structure effects were observed in the modeled structures 1a–6a to those observed for the x‐ray structures 1–6.
Details
- Title
- Structural studies on sulfonylbicyclo[n.2.0]alkan-1-ols
- Authors/Creators
- P.C. Healy (Author/Creator)W.A. Loughlin (Author/Creator)M.A. McCleary (Author/Creator)G.K. Pierens (Author/Creator)C.C. Rowen (Author/Creator)
- Publication Details
- Journal of Physical Organic Chemistry, Vol.15(11), pp.733-741
- Publisher
- John Wiley & Sons, Ltd
- Identifiers
- 991005545144007891
- Copyright
- © 2002 John Wiley & Sons, Ltd.
- Murdoch Affiliation
- Murdoch University
- Language
- English
- Resource Type
- Journal article
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- Citation topics
- 2 Chemistry
- 2.1 Synthesis
- 2.1.40 Total Synthesis
- Web Of Science research areas
- Chemistry, Organic
- Chemistry, Physical
- ESI research areas
- Chemistry