Ylide

A ylide is a neutral molecule with positive and negative charges on adjacent atoms. The most common ylides are used in the Wittig reaction for double bond synthesis from carbonyl groups (C=O). The positive charge is carried by a phosphorus atom with three phenyl substituents and one bond to a carbon bearing a negative charge and two substituents, commonly alkyl groups. Ylides can be 'stabilised' and 'non-stabilised', non stabilised react readily with both aldehydes and ketones whereas stabilised will only react with aldehydes.

 

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