Barton reaction
E395220
The Barton reaction is an organic photochemical transformation that converts nitrite esters into δ-nitroso alcohols via intramolecular hydrogen abstraction and radical rearrangement.
All labels observed (2)
| Label | Occurrences |
|---|---|
| Barton nitrite photolysis | 1 |
| Barton reaction canonical | 1 |
How this entity was disambiguated
This entity first appeared as the object of triple T3877955 — 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: Barton reaction Context triple: [Derek H. R. Barton, notableWork, Barton reaction]
-
A.
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.
-
B.
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.
-
C.
Fischer esterification
Fischer esterification is a classic acid-catalyzed organic reaction that forms esters from carboxylic acids and alcohols under reversible equilibrium conditions.
-
D.
Sharpless epoxidation
Sharpless epoxidation is a landmark asymmetric oxidation reaction in organic chemistry that enables the enantioselective conversion of allylic alcohols to epoxides using chiral catalysts.
-
E.
Beckmann
Beckmann is a German surname most famously associated with the Expressionist painter Max Beckmann.
- 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: Barton reaction Target entity description: The Barton reaction is an organic photochemical transformation that converts nitrite esters into δ-nitroso alcohols via intramolecular hydrogen abstraction and radical rearrangement.
-
A.
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.
-
B.
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.
-
C.
Fischer esterification
Fischer esterification is a classic acid-catalyzed organic reaction that forms esters from carboxylic acids and alcohols under reversible equilibrium conditions.
-
D.
Sharpless epoxidation
Sharpless epoxidation is a landmark asymmetric oxidation reaction in organic chemistry that enables the enantioselective conversion of allylic alcohols to epoxides using chiral catalysts.
-
E.
Beckmann
Beckmann is a German surname most famously associated with the Expressionist painter Max Beckmann.
- F. None of above. chosen
Statements (46)
| Predicate | Object |
|---|---|
| instanceOf |
organic reaction
ⓘ
photochemical reaction ⓘ radical reaction ⓘ |
| application |
remote functionalization of C–H bonds
ⓘ
steroid modification ⓘ synthesis of δ-amino alcohol derivatives via further transformations ⓘ |
| bondBroken | O–N bond of nitrite ester ⓘ |
| bondFormed |
C–N bond
ⓘ
N–O bond in nitroso group ⓘ |
| category | name reaction in organic chemistry ⓘ |
| discoveredBy | Derek H. R. Barton ⓘ |
| drivingForce |
formation of stable nitroso functionality
ⓘ
intramolecular radical recombination ⓘ |
| field |
organic chemistry
ⓘ
photochemistry ⓘ |
| involvesIntermediate |
alkoxy radical
ⓘ
carbon-centered radical ⓘ nitroso radical ⓘ |
| mechanismStep |
1,5-hydrogen abstraction
ⓘ
C–O bond homolysis ⓘ formation of alkoxy radical ⓘ formation of δ-carbon-centered radical ⓘ intramolecular hydrogen abstraction ⓘ photoexcitation of nitrite ester ⓘ radical rearrangement ⓘ recombination to form δ-nitroso alcohol ⓘ |
| namedAfter |
Derek H. R. Barton
ⓘ
surface form:
Sir Derek H. R. Barton
|
| product |
delta-nitroso alcohol
ⓘ
δ-nitroso alcohol ⓘ |
| reactant |
alkyl nitrite
ⓘ
nitrite ester ⓘ |
| reactionType |
1,5-hydrogen atom transfer
ⓘ
homolytic substitution ⓘ intramolecular reaction ⓘ |
| relatedReaction |
Barton reaction
self-linksurface differs
ⓘ
surface form:
Barton nitrite photolysis
Barton–McCombie deoxygenation ⓘ |
| requires |
light irradiation
ⓘ
ultraviolet light ⓘ |
| selectivity | prefers 1,5-hydrogen abstraction over more distant positions ⓘ |
| stereochemicalOutcome | can proceed with partial loss of stereochemistry at radical center ⓘ |
| typicalCondition |
inert atmosphere
ⓘ
non-polar organic solvent ⓘ |
| typicalSubstrate |
steroid nitrite esters
ⓘ
δ-functionalizable alcohols as nitrite esters ⓘ |
| usedFor | introduction of nitroso group at δ-position relative to hydroxyl group ⓘ |
| yearProposed | 1960s ⓘ |
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: Barton reaction Description of subject: The Barton reaction is an organic photochemical transformation that converts nitrite esters into δ-nitroso alcohols via intramolecular hydrogen abstraction and radical rearrangement.
Referenced by (2)
Full triples — surface form annotated when it differs from this entity's canonical label.
this entity surface form:
Barton nitrite photolysis