Synthesis of new water-soluble phosphonium salts and their Wittig reactions in water

2000 ◽  
pp. 505-513 ◽  
Author(s):  
Matthew G. Russell ◽  
Stuart Warren
Keyword(s):  
Water Soluble ◽  
Phosphonium Salts ◽  
Wittig Reactions

Hydrophobic Encapsulated Phosphonium Salts-Synthesis of Weakly Coordinating Cations and their Application in Wittig Reactions

2015 ◽  
Vol 21 (25) ◽  
pp. 9119-9125 ◽  
Author(s):  
Ralf Moritz ◽  
Manfred Wagner ◽  
Dieter Schollmeyer ◽  
Martin Baumgarten ◽  
Klaus Müllen
Keyword(s):  
Phosphonium Salts ◽  
Weakly Coordinating ◽  
Wittig Reactions

SYNTHESIS OF ISOTOPICALLY LABELLED OLEFINS VIA THE WITTIG REACTION

1965 ◽  
Vol 43 (5) ◽  
pp. 1614-1624 ◽  
Author(s):  
J. G. Atkinson ◽  
M. H. Fisher ◽  
D. Horley ◽  
A. T. Morse ◽  
R. S. Stuart ◽  
...  
Keyword(s):  
Molecular Weight ◽  
Dimethyl Sulfoxide ◽  
Wittig Reaction ◽  
Low Molecular Weight ◽  
Phosphonium Salts ◽  
Reaction Conditions ◽  
Selective Labelling ◽  
Wittig Reactions

A new application of the Wittig reaction to the preparation of olefins of low molecular weight which allows selective labelling in the vinyl or allyl positions with isotopes of hydrogen and carbon has been developed. Using the modification of the Wittig reaction introduced by E. J. Corey, in which a solution of the methylsulfinyl carbanion in dimethyl sulfoxide serves as the base, a series of olefins from C2 to C8 were synthesized. The synthesis was applied to the preparation of the following labelled compounds: 5-methylene-14C-bicyclo[2.2.1]hept-2-ene; propene-1-14C; 1-butene-1-14C; propene-1-d1; 2-methylpropene-1,1-d2; 2-methyl-d3-propene-3,3,3-d3; 2-methyl-2-butene-4,4,4-d3; 2-methyl-d3-2-butene-1,1,1-d3; methylene-d2-cyclohexane. For the synthesis of carbon-labelled olefins the reaction has few limitations since the intermediates and products are isotopically stable under the reaction conditions. Deuterium-labelled olefins can be obtained from deuterated formaldehyde or β-deuterated phosphonium salts, but α-deuteroketones and aldehydes and α-deuterophosphonium salts lose the isotope to the solvent.In all the Wittig reactions, benzene was formed as a by-product in 10–15% yield. The mechanism of benzene formation is probably analogous to that proposed by Seyferth involving the decomposition of a pentacovalent phosphorous intermediate.

scholarly journals Water-soluble phosphonium salts as supramolecular synthons

2013 ◽  
Vol 69 (a1) ◽  
pp. s544-s544
Author(s):  
Attila C. Bényei ◽  
T. Szarvas ◽  
A. Udvardy ◽  
Á. Kathó
Keyword(s):  
Water Soluble ◽  
Phosphonium Salts ◽  
Supramolecular Synthons

Water-soluble phosphonium salts containing 1,12-dicarba-closo-dodecaborane(12)

2009 ◽  
Vol 50 (47) ◽  
pp. 6457-6461 ◽  
Author(s):  
Joseph A. Ioppolo ◽  
Michael Kassiou ◽  
Louis M. Rendina
Keyword(s):  
Water Soluble ◽  
Phosphonium Salts
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