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Structural studies on sulfonylbicyclo[n.2.0]alkan-1-ols

Healy, P.C., Loughlin, W.A., McCleary, M.A., Pierens, G.K. and Rowen, C.C.ORCID: 0000-0003-4490-9542 (2002) Structural studies on sulfonylbicyclo[n.2.0]alkan-1-ols. Journal of Physical Organic Chemistry, 15 (11). pp. 733-741.

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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.

Item Type: Journal Article
Publisher: John Wiley & Sons, Ltd
Copyright: © 2002 John Wiley & Sons, Ltd.
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