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...

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Veröffentlicht in:Canadian journal of chemistry 1991-12, Vol.69 (12), p.1929-1939
Hauptverfasser: Kayser, Margaret M, Hatt, Krista L, Hooper, Donald L
Format: Artikel
Sprache:eng
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Zusammenfassung: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