Allylic proton-proton coupling in stereodefined alkylidenecyclobutanes and alkylidenecycopentanes


Allylic proton-proton coupling in stereodefined alkylidenecyclobutanes and alkylidenecycopentanes
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Timo V. Ovaska ;Journal of the Mexican Chemical Society 2009, 53 (3)
Autor: William F. Bailey
Fuente: http://www.redalyc.org/
Introducción
Journal of the Mexican Chemical Society
ISSN: 1870-249X
editor.jmcs@gmail.com
Sociedad Química de México
México
Bailey, William F.; Ovaska, Timo V.
Allylic Proton-Proton Coupling in Stereodefined Alkylidenecyclobutanes and Alkylidenecycopentanes
Journal of the Mexican Chemical Society, vol.
53, núm.
3, julio-septiembre, 2009, pp.
139-142
Sociedad Química de México
Distrito Federal, México
Available in: http:--www.redalyc.org-articulo.oa?id=47512154010
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J.
Mex.
Chem.
Soc.
2009, 53(3), 139-142
© 2009, Sociedad Química de México
ISSN 1870-249X
Article
Allylic Proton-Proton Coupling in Stereodefined Alkylidenecyclobutanes
and Alkylidenecycopentanes
William F.
Bailey1* and Timo V.
Ovaska2*
1
2
Department of Chemistry, The University of Connecticut, Storrs, Connecticut 06269-3060, USA.
William.Bailey@uconn.edu
Department of Chemistry, Connecticut College, New London, Connecticut 06320-4196, USA.
tvova@conncoll.edu
Dedicated to Professor Ernest L.
Eliel: a giant in the field of stereochemistry and to us a mentor and friend
to whom much is owed for his generous support and encouragement.
Received June 28, 2009; accepted August 14, 2009
Abstract.
Analysis of the 1H NMR spectra of eight stereodefined
alkylidenecycloalkanes allows determination of the magnitude of
allylic coupling in these compounds.
In contrast to the trend normally
observed, the magnitude of transoid-allylic coupling was found to
be invariably greater by ~0.5 Hz than the cisoid-allylic coupling.
The larger transoid-allylic coupling may be attributed to the slightly
smaller dihedral angle relating allylic =C–C–H plane with the C=C–C
plane in the E-isomers.
Keywords: Proton NMR, Allylic Coupling, Alkyliden...