Breslow intermediate
E601252
The Breslow intermediate is a reactive enaminol species proposed in organocatalysis that explains the umpolung (polarity inversion) of aldehydes in N-heterocyclic carbene-catalyzed reactions.
All labels observed (1)
| Label | Occurrences |
|---|---|
| Breslow intermediate canonical | 1 |
How this entity was disambiguated
This entity first appeared as the object of triple T6630434 — 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: Breslow intermediate Context triple: [Ronald Breslow, notableConcept, Breslow intermediate]
-
A.
Ann Arbor staging system
The Ann Arbor staging system is a clinical classification method used to determine the extent and spread of lymphomas, particularly Hodgkin and non-Hodgkin lymphomas, within the body.
-
B.
TNM
TNM is the IATA airport code for Teniente Rodolfo Marsh Martin Aerodrome, a Chilean airfield located on King George Island in Antarctica.
-
C.
Codman
Codman is a surname most notably associated with Ogden Codman Jr., an influential American architect and interior decorator of the late 19th and early 20th centuries.
-
D.
Hodgkin
Hodgkin is a surname most famously associated with Dorothy Hodgkin, the Nobel Prize–winning British chemist who advanced the field of X-ray crystallography.
-
E.
Leigh-Mallory
Leigh-Mallory is the surname of a prominent British military family, most notably borne by Air Chief Marshal Trafford Leigh-Mallory, a senior Royal Air Force commander during the Second World War.
- 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: Breslow intermediate Target entity description: The Breslow intermediate is a reactive enaminol species proposed in organocatalysis that explains the umpolung (polarity inversion) of aldehydes in N-heterocyclic carbene-catalyzed reactions.
-
A.
Ann Arbor staging system
The Ann Arbor staging system is a clinical classification method used to determine the extent and spread of lymphomas, particularly Hodgkin and non-Hodgkin lymphomas, within the body.
-
B.
TNM
TNM is the IATA airport code for Teniente Rodolfo Marsh Martin Aerodrome, a Chilean airfield located on King George Island in Antarctica.
-
C.
Codman
Codman is a surname most notably associated with Ogden Codman Jr., an influential American architect and interior decorator of the late 19th and early 20th centuries.
-
D.
Hodgkin
Hodgkin is a surname most famously associated with Dorothy Hodgkin, the Nobel Prize–winning British chemist who advanced the field of X-ray crystallography.
-
E.
Leigh-Mallory
Leigh-Mallory is the surname of a prominent British military family, most notably borne by Air Chief Marshal Trafford Leigh-Mallory, a senior Royal Air Force commander during the Second World War.
- F. None of above. chosen
Statements (47)
| Predicate | Object |
|---|---|
| instanceOf |
enaminol
ⓘ
organic chemical species ⓘ reaction intermediate ⓘ |
| explains | umpolung of aldehydes ⓘ |
| field |
organocatalysis
ⓘ
physical organic chemistry ⓘ reaction mechanism analysis ⓘ |
| formedBy |
addition of N-heterocyclic carbene to aldehyde carbonyl
ⓘ
subsequent proton transfer and tautomerization to an enaminol ⓘ |
| hasAlternativeName |
Breslow enaminol
ⓘ
NHC-bound enaminol intermediate ⓘ |
| hasComponent |
alpha-carbon bearing partial negative character
ⓘ
conjugated C=C–C=O system ⓘ enol hydroxyl group ⓘ |
| hasElectronicEffect | inverts electrophilic carbonyl carbon to nucleophilic center ⓘ |
| hasPrecursor |
N-heterocyclic carbene
ⓘ
aldehyde ⓘ |
| hasProperty |
can be stabilized in some systems for spectroscopic observation
ⓘ
highly reactive ⓘ nucleophilic at the former carbonyl carbon ⓘ often not directly observable ⓘ results from polarity inversion of aldehyde carbonyl ⓘ transient ⓘ |
| hasRole |
key intermediate in N-heterocyclic carbene catalysis
ⓘ
nucleophilic acyl anion equivalent ⓘ umpolung reagent ⓘ |
| isPartOf |
mechanism of Stetter reaction
ⓘ
mechanism of benzoin condensation ⓘ |
| mechanisticRole |
central intermediate in organocatalytic umpolung chemistry
ⓘ
connects N-heterocyclic carbene addition to aldehyde with acyl anion reactivity ⓘ |
| namedAfter | Ronald Breslow NERFINISHED ⓘ |
| occursIn | N-heterocyclic carbene organocatalytic cycles ⓘ |
| participatesIn |
N-heterocyclic carbene-catalyzed Stetter reaction
ⓘ
N-heterocyclic carbene-catalyzed acylation reactions ⓘ N-heterocyclic carbene-catalyzed benzoin condensation ⓘ N-heterocyclic carbene-catalyzed umpolung reactions of aldehydes ⓘ |
| proposedBy | Ronald Breslow NERFINISHED ⓘ |
| proposedIn | 1950s ⓘ |
| relatedTo |
N-heterocyclic carbene
ⓘ
Stetter reaction NERFINISHED ⓘ acyl anion equivalent ⓘ benzoin condensation ⓘ umpolung ⓘ |
| stabilizedBy |
conjugating substituents on the aldehyde
ⓘ
electron-withdrawing substituents on the N-heterocyclic carbene ⓘ |
| usedAsConceptIn |
design of new N-heterocyclic carbene catalysts
ⓘ
development of umpolung-based synthetic methods ⓘ |
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: Breslow intermediate Description of subject: The Breslow intermediate is a reactive enaminol species proposed in organocatalysis that explains the umpolung (polarity inversion) of aldehydes in N-heterocyclic carbene-catalyzed reactions.
Referenced by (1)
Full triples — surface form annotated when it differs from this entity's canonical label.