Publication

Phosphor-Betaine als Wittig-Zwischenstufen : Es gibt sie doch !

Manfred Schlosser
1977
Journal Articles

Abstract

Phosphorus ylides combine with carbonyl compds. to give zwitterionic betaines as detectable intermediates of the Wittig reaction, provided that the neg. charge on the O atom was substantially reduced by binding to a Li cation or resonance delocalization into an adjacent carbonyl group. Thus, Bu3P+Me I- was lithiated to give Bu3P+CH2-.LiI, which, with Ph2CO gave Bu3P+CH2CPh2OLi I- which, at room temp., decomposed to give Bu3PO and 1,1-diphenylethylene. Lithiation of Bu3P+CH2CPh2OH I- gave I. The reaction of Ph3P+C-Me2 with Ph2C:C:O, tert-butyl isocyanate, and CO2 gave II which was in equil. with Ph3P+CMe2C(:X)O- (X = CPh2, NCMe3, O). [on SciFinder (R)]

Official source

https://infoscience.epfl.ch/entities/publication/9719e73e-796d-4c28-8988-6a7af5928ca4

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Manfred Schlosser
1977
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/9719e73e-796d-4c28-8988-6a7af5928ca4

About this result

Related concepts (23)

Wittig reagents

In organic chemistry, Wittig reagents are organophosphorus compounds of the formula R3P=CHR', where R is usually phenyl. They are used to convert ketones and aldehydes to alkenes: Because they typically hydrolyze and oxidize readily, Wittig reagents are prepared using air-free techniques. They are typically generated and used in situ. THF is a typical solvent. Some are sufficiently stable to be sold commercially. Wittig reagents are usually prepared from a phosphonium salt, which is in turn prepared by the quaternization of triphenylphosphine with an alkyl halide.

Functional group

In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the rest of the molecule's composition. This enables systematic prediction of chemical reactions and behavior of chemical compounds and the design of chemical synthesis. The reactivity of a functional group can be modified by other functional groups nearby.

Carbonyl group

In organic chemistry, a carbonyl group is a functional group with the formula , composed of a carbon atom double-bonded to an oxygen atom, and it is divalent at the C atom. It is common to several classes of organic compounds (such as aldehydes, ketones and carboxylic acids), as part of many larger functional groups. A compound containing a carbonyl group is often referred to as a carbonyl compound. The term carbonyl can also refer to carbon monoxide as a ligand in an inorganic or organometallic complex (a metal carbonyl, e.

Related publications (1)

Phosphor-Betaine als Wittig-Zwischenstufen : Es gibt sie doch !

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New reagents to introduce weakly coordinating anions of type Al(ORF)4-: synthesis, structure and characterization of Cs and trityl salts