Triple

T16418898
Position Surface form Disambiguated ID Type / Status
Subject Eschenmoser–Claisen rearrangement E398759 entity
Predicate relatedTo P37 FINISHED
Object 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.
E1211457 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: Ireland–Claisen rearrangement | Statement: [Eschenmoser–Claisen rearrangement, relatedTo, Ireland–Claisen rearrangement]
NED1 Entity disambiguation (via context triple) gpt-5-mini-2025-08-07
Target entity: Ireland–Claisen rearrangement
Context triple: [Eschenmoser–Claisen rearrangement, relatedTo, Ireland–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. Corey–Nicolaou macrolactonization
    Corey–Nicolaou macrolactonization is a widely used organic synthesis reaction that forms large-ring lactones from hydroxy acids via an activated ester intermediate.
  • 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: Ireland–Claisen rearrangement
Triple: [Eschenmoser–Claisen rearrangement, relatedTo, Ireland–Claisen rearrangement]
Generated description
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.
NED2 Entity disambiguation (via description) gpt-5-mini-2025-08-07
Target entity: Ireland–Claisen rearrangement
Target entity description: 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.
  • 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. Corey–Nicolaou macrolactonization
    Corey–Nicolaou macrolactonization is a widely used organic synthesis reaction that forms large-ring lactones from hydroxy acids via an activated ester intermediate.
  • 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_6a003c6e882c81908fae034f1b75b7ee completed May 10, 2026, 8:06 a.m.
NEDg Description generation batch_6a003ed0bc7c8190b50e5f91cbdde6b7 completed May 10, 2026, 8:16 a.m.
NED2 Entity disambiguation (via description) batch_6a003f5eb85c81909aa101efccff7b86 completed May 10, 2026, 8:18 a.m.
Created at: April 10, 2026, 5:09 a.m.