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La configuration du «carquéjol» (Isopropényl‐2‐méthylène‐3‐cyclohexène‐4‐ol) et la conformation privilégiée de l' ortho‐néo‐isomenthol
Author(s) -
Thomas Alan F.
Publication year - 1967
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19670500320
Subject(s) - chemistry , methylene , isopropyl , stereochemistry , group (periodic table) , absolute configuration , circular dichroism , medicinal chemistry , organic chemistry
Abstract The complete stereochemistry of carquejol (= cis ‐(2 S )‐isopropenyl‐3‐methylene‐cyclohex‐4‐en‐1‐ol) is described. The absolute configuration was obtained from the circular dichroism of the corresponding 0 ‐menthones. Carquejol and its reduction products, having the all‐ cis configuration, appear from NMR. measurements to prefer a conformation having the hydroxyl (or acetoxyl) group axial and the isopropenyl (or isopropyl) group equatorial, even when the exo‐methylene group is reduced to methyl. The mass spectra of the compounds are briefly described.