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1H n.m.r. spectra of 6-acetoxy-2,4-cyclohexadienones

✍ Scribed by W. A. Bubb; C. J. Fallick; S. Sternhell

Publisher: John Wiley and Sons
Year: 1977
Tongue: English
Weight: 411 KB
Volume: 9
Category: Article
ISSN: 0749-1581
DOI: 10.1002/mrc.1270090314

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✦ Synopsis

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.

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