ylide
Sign in to saveAn ylide () or ylid () is a neutral dipolar molecule containing a formally negatively charged atom (usually a carbanion) directly attached to a heteroatom with a formal positive charge (usually nitrogen, phosphorus or sulfur), and in which both atoms have full octets of electrons. The result can be viewed as a structure in which two adjacent atoms are connected by both a covalent and an ionic bond; normally written X+–Y−. Ylides are thus 1,2-dipolar compounds, and a subclass of zwitterions. They appear in organic chemistry as reagents or reactive intermediates.
Article
15 sectionsContents
- Resonance structures
- Phosphonium ylides
- Non-symmetric phosphorus ylides
- Other types
- Based on sulfur
- Based on oxygen
- Based on nitrogen
- Other
- Reactions
- Dipolar cycloadditions
- Dehydrocoupling with silanes
- Sigmatropic rearrangements
- Allylic rearrangements
- See also
- References
An ylide () or ylid () is a neutral dipolar molecule containing a formally negatively charged atom (usually a carbanion) directly attached to a heteroatom with a formal positive charge (usually nitrogen, phosphorus or sulfur), and in which both atoms have full octets of electrons. The result can be viewed as a structure in which two adjacent atoms are connected by both a covalent and an ionic bond; normally written X+–Y−. Ylides are thus 1,2-dipolar compounds, and a subclass of zwitterions. They appear in organic chemistry as reagents or reactive intermediates.
The class name "ylide" for the compound should not be confused with the suffix "-ylide".