A neutral species with adjacent formally positive and negative centres. Ammonium ylides can undergo stereospecific [2,3]-sigmatropic rearrangements.
A charge-separated species with a nucleophilic carbon adjacent to positively charged sulfur. Conjugate addition followed by displacement of a sulfur leaving group can produce carbocycles or heterocycles.
A ylide with adjacent phosphorus-positive and carbon-negative descriptions, often represented by a phosphorane form. Its carbon can be coupled to a carbonyl carbon in Wittig olefination.
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