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Record W2514792048 · doi:10.1021/acs.orglett.6b02204

A Fresh Look at the Staudinger Reaction on Azido Esters: Formation of 2<i>H</i>-1,2,3-Triazol-4-ols from α-Azido Esters Using Trialkyl Phosphines

2016· article· en· W2514792048 on OpenAlexafffund
Scott D. Taylor, Chuda Raj Lohani

Bibliographic record

VenueOrganic Letters · 2016
Typearticle
Languageen
FieldChemistry
TopicClick Chemistry and Applications
Canadian institutionsUniversity of Waterloo
FundersNatural Sciences and Engineering Research Council of Canada
KeywordsChemistryPhosphoramidateYield (engineering)Reaction conditionsMedicinal chemistryTriazoleCombinatorial chemistryOrganic chemistryStereochemistryCatalysis

Abstract

fetched live from OpenAlex

Phenyl esters of α-azido acids react with trialkylphosphines in THF/H2O to give 5-substituted 2H-1,2,3-triazol-4-ols in good to excellent yields. In contrast, their reaction with PPh3 in THF/H2O give the amino esters as the major product and no triazoles. Reaction between an α-azido phenyl ester and P(OEt)3 provided the corresponding phosphoramidate in excellent yield, but no triazole was formed.

Fetched live from OpenAlex and de-inverted. Abstracts are not stored in this database: the inverted indexes are 8.6 GB of the frame’s 9.3 GB of text, and the host has 13 GB free.

How this classification was reachedexpand

Full frame machine prediction

Teacher imitation

Not calibrated prevalence, not ground truth. Human validation pending. The Gemma side is a direct model label for every work in the frame, read from the title-only record. The Codex side is a classifier learned from the 10,348 direct Codex labels and calibrated to design-weighted sample rates; fields without enough sample support carry no Codex call. Candidate is the union of the two sides; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels.

metaresearch head score (Codex)0.000
metaresearch head score (Gemma)0.000
Version: metacan-v3-hybrid-931329e0061cValidation status: machine_predicted_unvalidated
Candidate categoriesnone
Consensus categoriesnone
DomainCandidate signal: none · Consensus signal: none
Study designCandidate signal: Bench or experimental · Consensus signal: Bench or experimental
GenreCandidate signal: Empirical · Consensus signal: Empirical
Teacher disagreement score0.004
Threshold uncertainty score0.013

Distilled classifier scores by category (both heads)

CategoryCodexGemma
Metaresearch0.0000.000
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0000.000
Bibliometrics0.0000.000
Science and technology studies0.0000.000
Scholarly communication0.0010.001
Open science0.0000.000
Research integrity0.0000.001
Insufficient payload (model declined to judge)0.0040.002

Machine scores (provisional)

The two teacher heads of the student model, read on this work. A score orders the frame for review; it never asserts a category, and the validation status ships verbatim with every row.

Baseline scores from an immature model (maturity gate not passed, 7 training rounds). Scores rank; they never assert a category.

Opus teacher head0.024
GPT teacher head0.245
Teacher spread0.222 · how far apart the two teachers sit on this one work
Validation statusscore_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from it

Classification

machine, unvalidated

Machine predicted; a candidate call from one source (direct Gemma or distilled Codex), not a consensus.

The models applied no category: nothing in the taxonomy fit this work.
Study designBench or experimental
Domainnot available
GenreEmpirical

How this classification was reached, model by model and score by score, is at the end of the page under "How this classification was reached".

Quick stats

Citations20
Published2016
Admission routes2
Has abstractyes

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