Organic compound in which two atoms are connected by both a covalent and an ionic bond in resonance
An ylide (/ˈɪlaɪd/)[1] or ylid (/ˈɪlɪd/) 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.[2] They appear in organic chemistry as reagents or reactive intermediates.[3]
The class name "ylide" for the compound should not be confused with the suffix "-ylide".
An ylide (/ˈɪlaɪd/) or ylid (/ˈɪlɪd/) is a neutral dipolar molecule containing a formally negatively charged atom (usually a carbanion) directly attached...
chemical reaction of an aldehyde or ketone with a triphenyl phosphonium ylide called a Wittig reagent. Wittig reactions are most commonly used to convert...
Azomethine ylides are nitrogen-based 1,3-dipoles, consisting of an iminium ion next to a carbanion. They are used in 1,3-dipolar cycloaddition reactions...
Nitrile ylides also known as nitrilium ylides or nitrilium methylides, are generally reactive intermediates formally consisting of a carbanion of an alkyl...
15596-07-3) contains the C2O functionality. Sometimes called Bestmann's Ylide, it is a yellow solid. Frenking, Gernot; Tonner, Ralf "Divalent carbon(0)...
The Peterson olefination (also called the Peterson reaction) is the chemical reaction of α-silyl carbanions (1 in diagram below) with ketones (or aldehydes)...
charges on adjacent atoms is called an ylide, so sometimes the carbanion form of TPP is referred to as the "ylide form". In several reactions, including...
With reducing agents such as magnesium Wittig reaction Alkene Reagent: an ylide Takai reaction Alkene Diorganochromium reagent Corey–Fuchs reactions Alkyne...
skin. Cocamidopropyl betaine Mesoionic Mesomeric betaine Osmoprotectants Ylide "Betaine". PubChem, US National Library of Medicine. 21 August 2021. Retrieved...
Ylide chemistry. 1. Bifunctional acid-base-catalyzed conversion of heterosubstituted methanes into ethylene and derived hydrocarbons. The onium ylide...
mechanism of action of TPP as a coenzyme relies on its ability to form an ylide. Examples include: Present in most species pyruvate dehydrogenase and 2-oxoglutarate...
ylide in situ that reacts with enones, ketones, aldehydes, and imines to form corresponding epoxides, cyclopropanes, and aziridines. Two sulfur ylide...
phosphonium salt 7 with phenyl lithium to produce the phosphonium ylide 8. The ylide 8 is reacted with an aldehyde to produce the alkene 9. The ketal protecting...
the alkoxysulfonium ion to give the sulfur ylide 7. In a five-membered ring transition state, the sulfur ylide 7 decomposes to give dimethyl sulfide and...
(acetyl-transferring). The thiamine pyrophosphate (TPP) converts to an ylide by deprotonation. The ylide attack the ketone group of pyruvate. The resulting adduct...
with an electrophile gives a resonance stabilized cation With phosphonium ylides in the Wittig reaction to give the alkenes With thiols to give the thioacetal...
compound with the formula Ph3PCH2. It is the parent member of the phosphorus ylides, popularly known as Wittig reagents. It is a highly polar, highly basic...
Through a four-membered transition state, N2 is lost to form an aza-ylide. The unstable ylide is hydrolyzed to form phosphine oxide and a primary amine. However...
triphenylphosphine and the diethyl azodicarboxylate into one reagent: a phosphorane ylide. Both (cyanomethylene)trimethylphosphorane (CMMP, R = Me) and...
sulfonium and oxosulfonium salts affords ylides, of structure R2S+−C−−R′2 and R2S(O)+−C−−R′2. While sulfonium ylides, for instance in the Johnson–Corey–Chaykovsky...
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