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Record W4230398349 · doi:10.1002/047084289x.rm093.pub2

(Methoxycarbonylmethylene)triphenylphosphorane

2007· reference-entry· en· W4230398349 on OpenAlexaff
Allen B. Reitz, Mark E. McDonnell, Peter D. Wilson, Jeremy D. Pettigrew

Bibliographic record

VenueEncyclopedia of Reagents for Organic Synthesis · 2007
Typereference-entry
Languageen
FieldChemistry
TopicPhosphorus compounds and reactions
Canadian institutionsSimon Fraser University
Fundersnot available
KeywordsChemistryWittig reactionReagentPhosphoraneBromideAqueous solutionSolubilityNuclear chemistryMedicinal chemistryOrganic chemistry

Abstract

fetched live from OpenAlex

[2605-67-6] C21H19O2P (MW 334.37) InChI = 1S/C21H19O2P/c1-23-21(22)17-24(18-11-5-2-6-12-18,19-13-7-3-8-14-19)20-15-9-4-10-16-20/h2-17H,1H3 InChIKey = NTNUDYROPUKXNA-UHFFFAOYSA-N (stabilized phosphorane reagent useful for Wittig alkenation reactions to give methyl acrylate esters on reactions with carbonyl compounds1 and ozonides;2 formation of heterocyclic rings3) Alternate Name: methyl (triphenylphosphoranylidene)acetate. Physical Data: mp 169–171 °C. Solubility: sol CHCl3 (26 g 100 mL−1); slightly sol EtOH (2.7 g 100 mL−1), THF (3.8 g 100 mL−1); insol water (<0.5 g 100 mL−1). Form Supplied in: white crystalline powder; commercially available. Preparative Methods: readily prepared by mild base treatment of (methoxycarbonylmethyl)triphenylphosphonium bromide (pKa 8.8) (eq 1).4, 5 (1) Handling, Storage, and Precautions: storage at 5 °C in a tightly sealed bottle is recommended for prolonged periods. The compound decomposes to triphenylphosphine oxide in MeOH–water 1∶1 (t1/2 ca. 1.5 h) and in weakly basic aqueous solution (0.5 mM NaOH in MeOH–water 1∶1) (t1/2 ca. 1 h).

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: Not applicable · Consensus signal: none
GenreCandidate signal: Other · Consensus signal: none
Teacher disagreement score0.045
Threshold uncertainty score0.152

Distilled classifier scores by category (both heads)

CategoryCodexGemma
Metaresearch0.0000.000
Meta-epidemiology (narrow)0.0010.001
Meta-epidemiology (broad)0.0010.000
Bibliometrics0.0010.001
Science and technology studies0.0010.000
Scholarly communication0.0000.001
Open science0.0010.001
Research integrity0.0000.001
Insufficient payload (model declined to judge)0.0450.035

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 head0.019
GPT teacher head0.265
Teacher spread0.246 · 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 designNot applicable
Domainnot available
GenreOther

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".

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Citations0
Published2007
Admission routes1
Has abstractyes

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