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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.:

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

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

    Some are by both. E.g.:

    Others are not resonance stabilized. E.g.:

    see also Wittig reagent

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