A new generation of "instant ylides": powder mixtures of phosphonium salts and potassium hydride as storable precursors to Wittig reagents

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)]


Published in:
Tetrahedron Letters, 37, 50, 9047-9048
Year:
1996
Keywords:
Note:
CAN 126:103673
21-2
General Organic Chemistry
Batiment Chim.,Inst. Chim. Org. l'Univ.,Lausanne-Dorigny,Switz.
Journal
0040-4039
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\")
Laboratories:




 Record created 2006-03-03, last modified 2018-01-27


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