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Record W2165047237 · doi:10.1002/047084289x.rb075

Benzyl 3-(Tributylstannyl)acrylate

2001· reference-entry· en· W2165047237 on OpenAlexaff
Edward Piers, Christine Rogers

Bibliographic record

VenueEncyclopedia of Reagents for Organic Synthesis · 2001
Typereference-entry
Languageen
FieldChemistry
TopicOrganoboron and organosilicon chemistry
Canadian institutionsUniversity of British Columbia
Fundersnot available
KeywordsAcrylateMaterials scienceChemistryComposite materialCopolymerPolymer

Abstract

fetched live from OpenAlex

(E) [86633-19-4] C22H36O2Sn (MW 451.22) InChI = 1S/C10H9O2.3C4H9.Sn/c1-2-10(11)12-8-9-6-4-3-5-7-9;3*1-3-4-2;/h1-7H,8H2;3*1,3-4H2,2H3; InChIKey = YEQOWJFTRKWTLA-UHFFFAOYSA-N (Z) [86633-18-3] InChI = 1S/C10H9O2.3C4H9.Sn/c1-2-10(11)12-8-9-6-4-3-5-7-9;3*1-3-4-2;/h1-7H,8H2;3*1,3-4H2,2H3; InChIKey = YEQOWJFTRKWTLA-UHFFFAOYSA-N (this reagent, along with the corresponding ethyl and methyl esters, are useful partners for Pd0-catalyzed coupling reactions with a variety of substrates including aryl triflates,1-3 aryl bromides4 and iodides,5, 6 vinyl triflates,7, 8 vinyl iodides,9-13 allylic chlorides,14 acyl chlorides,15-17 and sulfonyl chlorides18) Physical Data: colorless oil. Solubility: sol THF, CHCl3. Preparative Methods: the benzyl acrylates 1 and 2 can be obtained by nonstereoselective hydrostannylation of benzyl propynoate (eq 1).15, 20 Mixtures of substances 3 and 410 and of 5 and 613, 21 have been prepared in similar fashion (eq 1). In each case the geometric isomers are chromatographically separable. The stereocontrolled synthesis of 3 can be achieved by sequential treatment of (E)-1,2-bis(tributylstannyl)ethene with an alkyllithium and ClCO2Et.22, 23 On the other hand, stereospecific syntheses of 5 and 6 have been achieved by reaction of methyl (E)- and (Z)-3-chloro (or iodo)acrylates with Bu3SnCu24 (see Tri‐n‐butylstannylcopper). (1) Handling, Storage, and Precautions: since organotin compounds are toxic,19 reactions preparing and employing the reagent should be carried out and worked up in a fume hood.

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 score0.051
Threshold uncertainty score0.170

Distilled classifier scores by category (both heads)

CategoryCodexGemma
Metaresearch0.0000.000
Meta-epidemiology (narrow)0.0010.000
Meta-epidemiology (broad)0.0000.000
Bibliometrics0.0000.001
Science and technology studies0.0000.000
Scholarly communication0.0000.000
Open science0.0010.000
Research integrity0.0000.001
Insufficient payload (model declined to judge)0.0510.030

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 head0.014
GPT teacher head0.244
Teacher spread0.229 · 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
Published2001
Admission routes1
Has abstractyes

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Same venueEncyclopedia of Reagents for Organic SynthesisSame topicOrganoboron and organosilicon chemistryFrench-language works237,207