Schrock carbene
E438047
A Schrock carbene is a type of organometallic complex featuring an early transition metal bonded to a strongly nucleophilic alkylidene ligand, central to many olefin metathesis catalysts.
All labels observed (1)
| Label | Occurrences |
|---|---|
| Schrock carbene canonical | 1 |
How this entity was disambiguated
This entity first appeared as the object of triple T4418987 — resolving that mention is where its identity was fixed. The disambiguator weighed these candidate entities and picked the highlighted one (or “None”, minting a new entity). This is how homonymy is resolved: the same surface form can point to different entities.
NED1
Entity disambiguation (via context triple)
gpt-5-mini-2025-08-07
Target entity: Schrock carbene Context triple: [Richard R. Schrock, notableConcept, Schrock carbene]
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A.
Eschenmoser
Eschenmoser is a Swiss surname most notably associated with Albert Eschenmoser, a prominent organic chemist known for his pioneering work in the synthesis of complex natural products and studies on the origin of life.
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B.
Eschenmoser sulfide contraction
Eschenmoser sulfide contraction is an organic rearrangement reaction that converts certain sulfur-containing intermediates into carbonyl compounds, widely used in complex molecule and natural product synthesis.
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C.
Eschenmoser–Claisen rearrangement
The Eschenmoser–Claisen rearrangement is a variant of the Claisen rearrangement in organic chemistry that converts allylic alcohols and amides into γ,δ-unsaturated carbonyl compounds via a [3,3]-sigmatropic rearrangement.
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D.
Suzuki coupling
Suzuki coupling is a widely used palladium-catalyzed cross-coupling reaction that forms carbon–carbon bonds between organoboron compounds and organic halides, fundamental in organic synthesis and pharmaceutical chemistry.
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E.
Buchwald–Hartwig amination
The Buchwald–Hartwig amination is a palladium-catalyzed cross-coupling reaction that forms carbon–nitrogen bonds by coupling aryl (or vinyl) halides with amines, widely used in the synthesis of pharmaceuticals and fine chemicals.
- F. None of above. chosen
- G. Unsure - the case is ambiguous/there is not enough information to decide.
NED2
Entity disambiguation (via description)
gpt-5-mini-2025-08-07
Target entity: Schrock carbene Target entity description: A Schrock carbene is a type of organometallic complex featuring an early transition metal bonded to a strongly nucleophilic alkylidene ligand, central to many olefin metathesis catalysts.
-
A.
Eschenmoser
Eschenmoser is a Swiss surname most notably associated with Albert Eschenmoser, a prominent organic chemist known for his pioneering work in the synthesis of complex natural products and studies on the origin of life.
-
B.
Eschenmoser sulfide contraction
Eschenmoser sulfide contraction is an organic rearrangement reaction that converts certain sulfur-containing intermediates into carbonyl compounds, widely used in complex molecule and natural product synthesis.
-
C.
Eschenmoser–Claisen rearrangement
The Eschenmoser–Claisen rearrangement is a variant of the Claisen rearrangement in organic chemistry that converts allylic alcohols and amides into γ,δ-unsaturated carbonyl compounds via a [3,3]-sigmatropic rearrangement.
-
D.
Suzuki coupling
Suzuki coupling is a widely used palladium-catalyzed cross-coupling reaction that forms carbon–carbon bonds between organoboron compounds and organic halides, fundamental in organic synthesis and pharmaceutical chemistry.
-
E.
Buchwald–Hartwig amination
The Buchwald–Hartwig amination is a palladium-catalyzed cross-coupling reaction that forms carbon–nitrogen bonds by coupling aryl (or vinyl) halides with amines, widely used in the synthesis of pharmaceuticals and fine chemicals.
- F. None of above. chosen
Statements (49)
| Predicate | Object |
|---|---|
| instanceOf |
alkylidene complex
ⓘ
carbene complex ⓘ organometallic complex ⓘ |
| contrastsWith | Fischer carbene NERFINISHED ⓘ |
| differsFromFischerCarbeneBy |
absence of strong π‑acceptor ligands like CO
ⓘ
early d0 metals instead of late low‑valent metals ⓘ nucleophilic rather than electrophilic carbene carbon ⓘ |
| discoveredBy | Richard R. Schrock NERFINISHED ⓘ |
| fieldOfStudy | organometallic chemistry ⓘ |
| hasBondingDescription |
π back‑donation from filled metal d orbitals is minimal
ⓘ
σ donation from carbanion‑like carbon to metal ⓘ |
| hasBondType | metal–carbon double bond ⓘ |
| hasCarbeneCarbonCharge | formally negative ⓘ |
| hasCarbeneCarbonGeometry | trigonal planar ⓘ |
| hasCarbeneCarbonHybridization | sp2 ⓘ |
| hasElectronicCharacter | nucleophilic carbene ⓘ |
| hasFormalOxidationStateOfMetal | high ⓘ |
| hasLigandType | alkylidene ligand ⓘ |
| hasMetalCarbonBondCharacter | polarized Mδ+–Cδ− ⓘ |
| hasMetalCenterType | early transition metal ⓘ |
| hasMetalElectronConfiguration | d0 ⓘ |
| hasReactivity |
can insert small molecules into M–C bond
ⓘ
reacts with carbonyl compounds to give metathesis or addition products ⓘ reacts with protic reagents to give alkanes or alcohols ⓘ |
| isKeyComponentOf | olefin metathesis catalysts ⓘ |
| mechanisticRole |
forms metallacyclobutane intermediates
ⓘ
mediates [2+2] cycloaddition with alkenes ⓘ undergoes cycloreversion to exchange alkylidene fragments ⓘ |
| namedAfter | Richard R. Schrock NERFINISHED ⓘ |
| participatesInReactionType |
alkene metathesis
ⓘ
olefin metathesis ⓘ |
| relatedAward | Nobel Prize in Chemistry 2005 (to Richard R. Schrock for work on olefin metathesis) NERFINISHED ⓘ |
| stability |
air‑sensitive
ⓘ
moisture‑sensitive ⓘ |
| typicalAncillaryLigands |
alkoxides
ⓘ
amido ligands ⓘ imido ligands ⓘ |
| typicalCarbeneSubstituents |
alkyl groups
ⓘ
aryl groups ⓘ |
| typicalMetal |
molybdenum
ⓘ
niobium ⓘ tantalum ⓘ tungsten ⓘ |
| typicalOxidationStatesOfMetal |
+4
ⓘ
+5 ⓘ +6 ⓘ |
| usedIn |
homogeneous catalysis
ⓘ
polymerization of olefins ⓘ synthesis of complex organic molecules ⓘ |
How these facts were elicited
The pipeline generated the facts above by prompting gpt-5.1 with this entity's name + description and the instruction below.
Instruction
You are a knowledge base construction expert. Given a subject entity and a description of it, return factual statements that you know for the subject as a JSON list of dictionaries(triples), where keys must be "subject", "predicate" and "object". The number of facts may be very high, between 25 to 50 or more, for very popular subjects. For less popular subjects, the number of facts can be very low, like 5 or 10. # Requirements - If you don't know the subject at all, return an empty list. - If the subject is not a named entity, return an empty list. - Include at least one triple where predicate is "instanceOf". - Do not get too wordy. - Separate several objects into multiple triples with one object.
Input
Subject: Schrock carbene Description of subject: A Schrock carbene is a type of organometallic complex featuring an early transition metal bonded to a strongly nucleophilic alkylidene ligand, central to many olefin metathesis catalysts.
Referenced by (1)
Full triples — surface form annotated when it differs from this entity's canonical label.