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1 H n.m.r. spectra of 6‐acetoxy‐2,4‐cyclohexadienones
Author(s) -
Bubb W. A.,
Fallick C. J.,
Sternhell S.
Publication year - 1977
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.1270090314
Subject(s) - substituent , benzene , chemistry , allylic rearrangement , ring (chemistry) , planarity testing , spectral line , carbon atom , medicinal chemistry , stereochemistry , ethylene , chemical shift , carbon fibers , crystallography , catalysis , organic chemistry , physics , materials science , astronomy , composite number , composite material
Abstract 1 H n.m.r. spectra of 36 derivatives of 6‐acetoxy‐2,4‐cyclohexadienones were analysed. All available evidence indicates that all members of the series have similar conformations which do not depart significantly from planarity. Substituent‐induced chemical shifts and interproton coupling constants correlate well with those in the analogously substituted ethylene and benzene derivatives. In particular, it appears that a substituent on the central carbon atom exerts a similar influence on 4 J (HH) across a ‘W’ path when the three intervening carbon atoms are a part of a benzene ring, an allylic system (i.e. sp 3 –sp 2 –sp 2 ), a localized sp 2 –sp 2 –sp 2 system or a saturated (i.e. sp 3 –sp 3 –sp 3 ) system.