The mixture of carquejanols obtained from carquejol of carqueja oil has been converted in ketones. The alkohols obtained respectively by hydrogenation on Pt(O2), by lithium‐aluminiumhydride reduction and by Meerwein‐Ponndorf‐Verley reaction have been separated by vapour phase chromatography. The ketones obtained from the Beckmann oxidation of the alkohols has been identified as carquejanone and isocarquejanone by application of the Auwers‐Skita rule.
The alcohols (+)‐carquejanol, (−)‐neocarquejanol, (−)‐isocarquejanol, and (−)‐neoisocarquejanol are described, and their conformations and configurations are studied by IR., NMR. and mass spectroscopies. Isocarquejanol is a mixture of conformers approximatively 50:50 with, respectively, axial and equatorial OH.
Die Konformationen und Konfigurationen von (+)‐Carquejanol (I), (‐)‐Neocarque′janol (II), (‐)‐Neoisocarque′janol (III) und (‐)‐Isocarquejanol (IV) werden IR‐, NMR‐ sowie massenspektrometrisch bestimmt.
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