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The stereochemistry of the 6‐membered ring of cedranone
Author(s) -
Rodríguez Mario,
Bertrán José Fernández
Publication year - 1980
Publication title -
organic magnetic resonance
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0030-4921
DOI - 10.1002/mrc.1270130408
Subject(s) - ring (chemistry) , cyclohexanone , chemistry , cyclohexane conformation , solvent , coupling constant , chemical shift , stereochemistry , crystallography , computational chemistry , molecule , organic chemistry , physics , hydrogen bond , particle physics , catalysis
Abstract Evidence from the coupling constants and solvent shifts of the protons in cedranone rules out the boat and chair conformations of the cyclohexanone ring. Linear correlation of the solvent shifts of the C‐15 methyl protons of cedranone with those of the α‐methyl groups of fenchone indicates a nearly planar conformation of the cedranone ring. Site factor analysis of the ASIS effect of the methyl protons of cedranone provides conclusive evidence of a quasi‐chair conformation of the 6‐membered ring.