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Die absolute Konfiguration von Carquejol und verwandten o ‐Menthan‐Derivaten
Author(s) -
Snatzke G.,
Thomas A. F.,
Ohloff G.
Publication year - 1969
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.19690520511
Subject(s) - chemistry , absolute configuration , stereochemistry , chirality (physics) , double bond , organic chemistry , chiral symmetry , physics , quantum mechanics , nambu–jona lasinio model , quark
The structure of carquejol is amended to that of cis ‐3‐hydroxy‐ o ‐mentha‐1(7),4,8‐triene; the chirality has been confirmed as 2 R , 3 S by correlation with the (−)‐ cis ‐ o ‐menthane obtained from carquejol and that from (+)‐verbenene of known absolute configuration. The two double bonds of the dihydrocarquejol system ( 15 and 16 ) constitute a helical system, that especially in the case of the acetate ( 16 ) fixes the isopropenyl group in such a way that a very high Δϵ value in the CD. curve is observed. The conformational significance of this phenomenon is discussed.