MétaCan
Menu
Back to cohort

Tri-<i>tert</i>-butylphosphine

2015· reference-entry· he· W1913076043 on OpenAlexaff
Kevin H. Shaughnessy, Francis Pinsonneault, Alexandre Gagnon

Bibliographic record

VenueEncyclopedia of Reagents for Organic Synthesis · 2015
Typereference-entry
Languagehe
FieldChemistry
TopicCatalytic Cross-Coupling Reactions
Canadian institutionsUniversité du Québec à Montréal
Fundersnot available
KeywordsOxidizing agentChemistryInert gasSolubilitySalt (chemistry)OxygenTorrInorganic chemistryOxideOrganic chemistry

Abstract

fetched live from OpenAlex

[12716-12-6] C12H27P (MW 202.32) 1S/C12H27P/c1-10(2,3)13(11(4,5)6)12(7,8)9/h1-9H3 InChIKey = BWHDROKFUHTORW-UHFFFAOYSA-N (supporting ligand for palladium-1 and rhodium-catalyzed2 cross-coupling reactions) Physical Data: mp 30 °C; bp 102–103 °C/13 Torr; d 0.812 g cm−3. Solubility: sol in most organic solvents; insol in H2O. Form Supplied: colorless liquid or low-melting solid; approx. 10%(w/w) solution in hexane; or as HBF4 salt as a white solid; widely available in all forms. Purification: by vacuum distillation (102–103 °C, 13 Torr). Handling, Storage, and Precautions: the pure material is pyrophoric and must be handled under an oxygen-free atmosphere to avoid spontaneous combustion. In the absence of oxygen, it is indefinitely stable. Solutions (ca. 10%) of tri-tert-butylphosphine are not pyrophoric, but should be handled under an inert atmosphere in order to avoid oxidation to the phosphine oxide. The HBF4 salt is air-stable. Tri-tert-butylphosphine is corrosive and causes burns on contact with skin. It is incompatible with oxidizing agents.

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 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)0.011
Version: codex-gemma-dda1882f352aValidation status: machine_predicted_unvalidated
Candidate categoriesMetaresearch, Meta-epidemiology (narrow), Research integrity, Insufficient payload (model declined to judge)
Consensus categoriesMeta-epidemiology (narrow), Insufficient payload (model declined to judge)
DomainCandidate signal: none · Consensus signal: none
Study designCandidate signal: Not applicable · Consensus signal: Not applicable
GenreCandidate signal: Other · Consensus signal: none
Teacher disagreement score0.336
Threshold uncertainty score0.999

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0010.011
Meta-epidemiology (narrow)0.0020.002
Meta-epidemiology (broad)0.0030.002
Bibliometrics0.0000.001
Science and technology studies0.0000.001
Scholarly communication0.0000.000
Open science0.0020.001
Research integrity0.0020.001
Insufficient payload (model declined to judge)0.0230.002

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 head0.026
GPT teacher head0.280
Teacher spread0.255 · 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; both teacher heads agree on what is shown here.

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".

Quick stats

Citations0
Published2015
Admission routes1
Has abstractyes

Explore more

Same venueEncyclopedia of Reagents for Organic SynthesisSame topicCatalytic Cross-Coupling ReactionsFrench-language works237,207