Triple

T16418897
Position Surface form Disambiguated ID Type / Status
Subject Eschenmoser–Claisen rearrangement E398759 entity
Predicate relatedTo P37 FINISHED
Object Claisen rearrangement
The Claisen rearrangement is a pericyclic [3,3]-sigmatropic rearrangement in organic chemistry that converts allyl vinyl ethers (or related systems) into γ,δ-unsaturated carbonyl compounds with high stereospecificity.
E1214434 NE FINISHED

How this triple was built (4 steps)

Every LLM step that produced this triple, in pipeline order — named-entity classification, the disambiguation choices (the exact options shown, with the pick highlighted), and the generated description. The batch + timestamp of each is in the Provenance table below.

NER Named-entity recognition gpt-5-mini
Instruction
Given a phrase, classify it is english named entity (e.g., persons, organizations, works of art) in Latin script, or not (e.g., literals, dates, URLs, verbose phrases). For disambiguation, the statement where the phrase occurs as object is also given. Please return a JSON object with `phrase` (string, the phrase being analyzed) and `is_ne` (boolean, indicating whether the phrase is a Named Entity).
Input
Phrase: Claisen rearrangement | Statement: [Eschenmoser–Claisen rearrangement, relatedTo, Claisen rearrangement]
NED1 Entity disambiguation (via context triple) gpt-5-mini-2025-08-07
Target entity: Claisen rearrangement
Context triple: [Eschenmoser–Claisen rearrangement, relatedTo, Claisen rearrangement]
  • A. 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.
  • B. Stork–Danheiser rearrangement
    The Stork–Danheiser rearrangement is an organic reaction that transforms certain allylic alcohol derivatives into rearranged carbonyl compounds via a sigmatropic shift, widely used in complex molecule synthesis.
  • C. Arbuzov rearrangement
    The Arbuzov rearrangement is an organic reaction in which trialkyl or triaryl phosphites react with alkyl halides to form phosphonates, widely used in the synthesis of organophosphorus compounds.
  • D. Overman rearrangement
    The Overman rearrangement is an organic chemical reaction that converts allylic alcohol derivatives into allylic amines via a [3,3]-sigmatropic rearrangement of allylic trichloroacetimidates.
  • E. Ireland–Claisen rearrangement
    The Ireland–Claisen rearrangement is a variant of the Claisen rearrangement in which an ester enolate undergoes a [3,3]-sigmatropic rearrangement to form γ,δ-unsaturated carboxylic acids with high stereocontrol.
  • F. None of above. chosen
  • G. Unsure - the case is ambiguous/there is not enough information to decide.
NEDg Description generation gpt-5.1
Instruction
Generate a one-sentence description of the target entity. 
You are given a context triple in the form (subject, predicate, object), where the object is the target entity. 
# Instructions
Use the triple to infer relevant information about the entity. Describe the entity based on what is most defining, well-known. 
Avoid repeating the information from the triple, unless really essential.
# Response Format
Return only the sentence: "Description: [one-sentence description of the target entity]"
Input
Entity: Claisen rearrangement
Triple: [Eschenmoser–Claisen rearrangement, relatedTo, Claisen rearrangement]
Generated description
The Claisen rearrangement is a pericyclic [3,3]-sigmatropic rearrangement in organic chemistry that converts allyl vinyl ethers (or related systems) into γ,δ-unsaturated carbonyl compounds with high stereospecificity.
NED2 Entity disambiguation (via description) gpt-5-mini-2025-08-07
Target entity: Claisen rearrangement
Target entity description: The Claisen rearrangement is a pericyclic [3,3]-sigmatropic rearrangement in organic chemistry that converts allyl vinyl ethers (or related systems) into γ,δ-unsaturated carbonyl compounds with high stereospecificity.
  • A. 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.
  • B. Stork–Danheiser rearrangement
    The Stork–Danheiser rearrangement is an organic reaction that transforms certain allylic alcohol derivatives into rearranged carbonyl compounds via a sigmatropic shift, widely used in complex molecule synthesis.
  • C. Arbuzov rearrangement
    The Arbuzov rearrangement is an organic reaction in which trialkyl or triaryl phosphites react with alkyl halides to form phosphonates, widely used in the synthesis of organophosphorus compounds.
  • D. Overman rearrangement
    The Overman rearrangement is an organic chemical reaction that converts allylic alcohol derivatives into allylic amines via a [3,3]-sigmatropic rearrangement of allylic trichloroacetimidates.
  • E. Ireland–Claisen rearrangement
    The Ireland–Claisen rearrangement is a variant of the Claisen rearrangement in which an ester enolate undergoes a [3,3]-sigmatropic rearrangement to form γ,δ-unsaturated carboxylic acids with high stereocontrol.
  • F. None of above. chosen

Provenance (5 batches)

The batch behind each pipeline step, in order, with when it ran. Timestamps are batch-level — stages were processed in waves, so the object chain (NER → NED1 → NEDg → NED2) reads in order, but predicate / elicitation batches can sit in a different wave.

Step Stage Batch ID Status When
creating Elicitation batch_69d87f2b9024819085c20e52de95d583 completed April 10, 2026, 4:40 a.m.
NER Named-entity recognition batch_69e3287a3d348190831b12101d8449b6 completed April 18, 2026, 6:45 a.m.
NED1 Entity disambiguation (via context triple) batch_6a004f457b8c8190b278697ef43301cb completed May 10, 2026, 9:26 a.m.
NEDg Description generation batch_6a004ff9e2e88190afa4726e3ba71ea9 completed May 10, 2026, 9:29 a.m.
NED2 Entity disambiguation (via description) batch_6a00505beaa881909aca531af1149fbc completed May 10, 2026, 9:31 a.m.
Created at: April 10, 2026, 5:09 a.m.