Mixing a finely pulverized alkyltriphenylphosphonium salt and potassium hydride in 1:1 molar ratio gives a ready-to-use powder the components of which react rapidly when tert-Bu Me ether is added under stirring. When, in general after a few minutes, the generation of the (triphenylphosphonio)alkanide is complete, it can be immediately used for the Wittig olefination of a carbonyl compd. Compared to sodium amide based \"instant ylides\", the new blends offer little advantage as long as simple phosphonium salts are ingredients but they extend considerably the shelf life of mixts. contg. heterosubstituted derivs. such as methylthiomethyl- or picolyltriphenylphosphonium salts. [on SciFinder (R)]
Title
A new generation of "instant ylides": powder mixtures of phosphonium salts and potassium hydride as storable precursors to Wittig reagents
Published in
Tetrahedron Letters
Volume
37
Issue
50
Pages
9047-9048
Date
1996
ISSN
0040-4039
Note
CAN 126:103673
21-2
General Organic Chemistry
Batiment Chim.,Inst. Chim. Org. l'Univ.,Lausanne-Dorigny,Switz.
Journal
written in English.
100-42-5 (Styrene); 100-52-7 (Benzaldehyde); 103-31-1 (4-Styrylpyridine); 351-78-0 ((2-Fluorovinyl)benzene); 622-25-3 (b-Chlorostyrene); 637-50-3 (1-Phenylpropene); 714-08-9 (2-Styrylpyridine); 1608-28-2; 2633-06-9 (3-Styrylpyridine); 2687-12-9; 4747-15-3 ((2-Methoxyvinyl)benzene); 7715-02-8 ([2-(Methylthio)vinyl]benzene); 10276-15-0 (1-Methylthio-3-phenyl-2-propene); 15314-20-2 (4-Methyl-1-phenylpentene); 16277-67-1; 70353-93-4 (1-Fluoro-3-phenyl-2-propene); 96090-09-4 (3-Cinnamylpyridine); 111678-19-4 (4-Cinnamylpyridine); 186032-39-3 (2-Cinnamylpyridine) Role: RCT (Reactant), RACT (Reactant or reagent) (Wittig reaction with \"instant ylide\")
Record creation date
2006-03-03
