MétaCan
Menu
Back to cohort
Record W4230398349 · doi:10.1002/047084289x.rm093.pub2

(Methoxycarbonylmethylene)triphenylphosphorane

2007· reference-entry· en· W4230398349 on OpenAlex

Why this work is in the frame

A frame that forgets how it found something cannot be audited. These are the routes that admitted this work.

affAt least one author lists a Canadian institution in the pinned OpenAlex snapshot.

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.

Full frame distilled prediction

Teacher imitation

Not calibrated prevalence, not ground truth. Human validation pending. Learned from the 10,348 direct Codex labels and 10,348 direct Gemma labels. Candidate is the union of thresholded teacher heads; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels or direct frontier model labels.

metaresearch head score (Codex)0.001
metaresearch head score (Gemma)0.002
Version: codex-gemma-dda1882f352aValidation status: machine_predicted_unvalidated
Candidate categoriesMeta-epidemiology (narrow), Research integrity, Insufficient payload (model declined to judge)
Consensus categoriesnone
DomainCandidate signal: none · Consensus signal: none
Study designCandidate signal: Not applicable · Consensus signal: none
GenreCandidate signal: Other · Consensus signal: Other
Teacher disagreement score0.702
Threshold uncertainty score1.000

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0010.002
Meta-epidemiology (narrow)0.0010.001
Meta-epidemiology (broad)0.0020.001
Bibliometrics0.0000.001
Science and technology studies0.0000.000
Scholarly communication0.0000.000
Open science0.0010.000
Research integrity0.0020.001
Insufficient payload (model declined to judge)0.0110.000

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