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- W1988948822 abstract "Die Solvomercurierungsreaktion der Cyclohexenole 3 und 4 liefert die cis/trans-Diole 1a bzw. reines trans-Diol 2a. Über die Monotosylate lassen sich das cis-Diol 2a sowie die cis-Aminoalkohole 1b und 2b diastereomerenrein durch SN2-Reaktionen mit KHCO3/18-Krone-6 bzw. KN3/18-Krone-6 und Reduktion mit LiAlH4 in guten Ausbeuten herstellen. NMR-spektroskopische Untersuchungen zeigen, daß in der cis-Reihe in aprotischen Medien die bisaxialen (cis-1-sc-sc) bzw. trisaxialen (cis-2-sc-sc) Konformationen – stabilisiert durch intramolekulare H-Brücken – vorliegen, während in protischen Medien die jeweiligen inversen Sesselkonformationen (cis-1-ap-ap bzw. cis-2-ap-ap) dominieren. Die konformativen Wechselwirkungen in den höher substituierten Cyclohexanderivaten 2 werden durch Röntgenstrukturanalyse eines cis- (cis-2b) und eines trans-Vertreters (trans-2a) untersucht. Syntheses and Conformational Properties of Stereoisomeric 1,3-Cyclohexanediol and 3-Aminocyclohexanol Derivatives. X-Ray Structure Analysis of trans-1,3-Dihydroxy-1,5,5-trimethylcyclohexane and c-3-Amino-r-1-hydroxy-1,5,5-trimethylcyclohexane Solvomercuration of cyclohexenols 3 and 4 yields the respective cis/trans-diols 1a and pure trans-diol 2a. Via the monotosylates the analogous cis-diol cis-2a as well as the cis-amino alcohols cis-1b and cis-2b are prepared diastereomerically pure in good yields by SN2 reaction with KHCO3/18-crown-6 and KN3/18-crown-6, resp., followed by LiAlH4 reduction. NMR spectroscopic investigations show that in the cis-series the bisaxial (cis-1-sc-sc) or the trisaxial (cis-2-sc-sc) conformations – stabilized by an intramolecular H-bond – exist in aprotic solvents, while in protic media the inverted chair conformations (cis-1-ap-ap and cis-2-ap-ap) dominate. The conformational interactions in the higher substituted compounds 2 are investigated by X-ray structure analyses of a cis (cis-2b) and a trans (trans-2a) representative." @default.
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- W1988948822 title "Synthese und konformative Eigenschaften stereoisomerer 1,3‐Cyclohexandiol‐ und 3‐Aminocyclohexanol‐Derivate. Röntgenstrukturanalyse von <i>trans</i> ‐1,3‐Dihydroxy‐1,5,5‐trimethylcyclohexan und <i>c</i> ‐3‐Amino‐ <i>r</i> ‐1‐hydroxy‐1,5,5‐trimethylcyclohexan" @default.
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- W1988948822 doi "https://doi.org/10.1002/cber.19851181104" @default.
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