Abstract
It is possible to remove a proton from the methyl group of a tetramethylphosphonium halide with strong bases. Thereby, a betaine (see Section 4.7.3) is produced with the structure Me3P⊕-CH2 ⊖. A betaine in which the positive and the negative charges are located on adjacent atoms as in Me3P⊕-CH2 ⊖ is called an ylide. The “yl” part of the name ylide refers to the covalent bond in the substructure P⊕-CH2 ⊖. The “ide” part indicates that it also contains an ionic bond. The ylide Me3P⊕-CH2 ⊖ is the parent compound of the phosphonium ylides or P ylides R1R2R3P⊕-CR4R5 ⊖. This terminology is used to distinguish them from other ylides like ammonium ylides or N ylides R1R2R3N⊕-CR4R5 ⊖ and sulfur ylides or S ylides R1R2S⊕-CR3R4⊖. With strong bases it is also possible to remove a proton from the methyl group of triarylmethylphosphonium halides to form the ylides Ar3P⊕-CR4R5⊖.
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(2010). Conversion of Phosphorus- or Sulfur-Stabilized C Nucleophiles with Carbonyl Compounds: Addition-induced Condensations. In: Harmata, M. (eds) Organic Mechanisms. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-03651-4_11
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