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Saturation transfer and chemical exchange measurements of the stereochemical drift occurring during the Wittig reaction
Author(s) -
Pascariu Aurelia,
Mracec Mircea,
Berger Stefan
Publication year - 2005
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.1573
Subject(s) - chemistry , wittig reaction , homonuclear molecule , benzaldehyde , saturation (graph theory) , analytical chemistry (journal) , organic chemistry , catalysis , molecule , mathematics , combinatorics
The Wittig reaction of butylidenetriphenylphosphorane with benzaldehyde using LiHMDS as base in THF was studied. The stereochemical drift (different ratio obtained in alkenes versus oxaphosphetane intermediates) was followed by low‐temperature 1D NMR techniques. A retro‐Wittig reaction is demonstrated using 13 C and 31 P saturation transfer experiments and homonuclear DPFGSE‐ROE techniques. Copyright © 2005 John Wiley & Sons, Ltd.