An NMR study of the structure and reactivity of phosphonium ylides stabilized by a carbonyl function

The structures of five stabilized phosphonium ylides 1 - 5 were studied by 1 H, 13 C, and 31 P NMR. Various trapping experiments were followed by investigation of the relative reactivities of these ylides vis-à-vis benzaldehyde. A novel effect of some significance, the influence of acidic contaminan...

Full description

Saved in:
Bibliographic Details
Published inCanadian journal of chemistry Vol. 69; no. 12; pp. 1929 - 1939
Main Authors Kayser, Margaret M, Hatt, Krista L, Hooper, Donald L
Format Journal Article
LanguageEnglish
Published Ottawa, Canada NRC Research Press 01.12.1991
National Research Council of Canada
Subjects
Chemistry
Exact sciences and technology
Organic chemistry
Organometalloidal and organometallic compounds
P derivatives
Preparations and properties
Trapping
Temperature
Benzaldehyde
Chemical reactivity
NMR spectrum
Phosphorus Organic compounds
Alkylation
Two dimension spectrometry
Ylide
Online AccessGet full text

Cover

More Information
Summary:The structures of five stabilized phosphonium ylides 1 - 5 were studied by 1 H, 13 C, and 31 P NMR. Various trapping experiments were followed by investigation of the relative reactivities of these ylides vis-à-vis benzaldehyde. A novel effect of some significance, the influence of acidic contaminants (conjugate acids, H 2 O, etc.) on the structure and reactivity of these compounds, is discussed. Key words: stabilized phosphoranes, Wittig condensations, acid catalysis.
ISSN:0008-4042
1480-3291
DOI:10.1139/v91-278