Title: Structure and properties of phosphonium ylides-betaines, derivatives of 2-phenyl-2-oxazolin-5-one and its thio-analogs and seleno-analogs
Authors: Van Meervelt, Luc ×
Schuerman, Gs
Brovarets, Vs
Mishchenko, Ni
Romanenko, Ea
Drach, Bs #
Issue Date: Jan-1995
Publisher: Pergamon-elsevier science ltd
Series Title: Tetrahedron vol:51 issue:5 pages:1471-1482
Abstract: The combined chemical, spectral, and X-ray structural investigation has shown that the structure and properties of mesomeric triphenylphosphonium ylides containing the 5-oxo-2-phenyl-4-oxazolidene moiety undergo considerable changes when the carbonyl oxygen atom is replaced by sulfur or selenium, This substitution leads to a clear decrease of the contribution of the ylide structure and an increased importance of the betaine structure, in contradiction with the electronegativity decrease in the O>S>Se series, but relates to the different ability of double bond formation of these elements. The deactivation of the ylide site by the thio- or selenocarbonyl group has been applied to regioselective syntheses.
ISSN: 0040-4020
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Biochemistry, Molecular and Structural Biology Section
× corresponding author
# (joint) last author

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