Ylide

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.

eg:



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

eg:



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

eg:



Some are by both.

eg:



Others are not resonance stabilized.

eg:



see also Wittig reagent

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