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YlideA ylid or ylide (US) is a neutral molecule with a positive and a negative charge on adjacent atoms. They appear in organic chemistry as reagents or reactive intermediates. Additional recommended knowledgeA ylide is accompanied to some extent by (and often depicted as) its double bonded resonance structure: The actual electron distribution in the bond depends on the entire molecular structure. Ylide types
Ylide reactionsAn important ylide reaction is of course the Wittig reaction but there are more. Many ylids are 1,3-dipoles and interact in 1,3-dipolar cycloadditions. For instance an azomethine ylid is a dipole in the Prato reaction with fullerenes. Many ylids also react as olefins in rearrangement reactions such as a [3,3]-sigmatropic reaction observed in certain phosphonium ylids [1] [2] Wittig reagents are found to react as nucleophiles in SN2' substitution [3]: The initial addition reaction is followed by an elimination reaction. References
Categories: Chemical nomenclature | Functional groups |
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Ylide". A list of authors is available in Wikipedia. |