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Chemistry LibreTexts

Ylide

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A ylide is a neutral species in which there is a carbon atom bearing a formal charge of -1 bound to a heteroatom bearing a formal charge of +1. Ylides are classified based on the nature of the positively charged heteroatom. E.g.:

ylide1.png

Some ylides are resonance stabilized due to pπ-dπ interactions. E.g.:

ylide2.png

Some are by delocalization of the lone pair on the negatively charged carbon atom to a pi bond. E.g.:

ylide3.png

Some are by both. E.g.:

ylide4.png

Others are not resonance stabilized. E.g.:

ylide5.png

see also Wittig reagent


This page titled Ylide is shared under a All Rights Reserved (used with permission) license and was authored, remixed, and/or curated by Gamini Gunawardena via source content that was edited to the style and standards of the LibreTexts platform.

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