Barton reaction

E395220

organic reaction photochemical reaction radical reaction

The Barton reaction is an organic photochemical transformation that converts nitrite esters into δ-nitroso alcohols via intramolecular hydrogen abstraction and radical rearrangement.

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All labels observed (2)

Label	Occurrences
Barton nitrite photolysis	1
Barton reaction canonical	1

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.

Derek H. R. Barton → notableWork → Barton reaction ⓘ

Barton reaction → relatedReaction → Barton reaction self-linksurface differs ⓘ

this entity surface form: Barton nitrite photolysis