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Record W1913796958 · doi:10.1002/047084289x.rc161

4-Chloro-2-trimethylstannyl-1-butene

2001· reference-entry· en· W1913796958 on OpenAlexaff
Edward Piers, Christine Rogers

Bibliographic record

VenueEncyclopedia of Reagents for Organic Synthesis · 2001
Typereference-entry
Languageen
FieldChemistry
TopicCoordination Chemistry and Organometallics
Canadian institutionsUniversity of British Columbia
Fundersnot available
KeywordsReagentChemistryDistillationBifunctionalSolubility2-ButeneOrganic chemistryCatalysis

Abstract

fetched live from OpenAlex

[85370-32-7] C7H15ClSn (MW 253.34) InChI = 1S/C4H6Cl.3CH3.Sn/c1-2-3-4-5;;;;/h1,3-4H2;3*1H3; InChIKey = CRTSSODYJHOAGQ-UHFFFAOYSA-N (precursor of a number of bifunctional reagents,1, 2 which have been employed for effecting synthetically useful methylenecyclopentane annulation sequences1-4) Physical Data: colorless liquid, distillation temperature (bulb-to-bulb) 55–60 °C/12 mmHg. Solubility: insol H2O; sol THF, Et2O, CHCl3, and other common organic solvents. Preparative Methods: 4-chloro-2-trimethylstannyl-1-butene 3 is readily prepared from the commercially available butynol 1. Regioselective addition of Me3SnCu·Me2S5 (see Trimethylstannylcopper–Dimethyl Sulfide) to 1 provides6 3-trimethylstannyl-3-buten-1-ol 2, which upon reaction with Ph3P–CCl4 in the presence of Et3N affords 3 (eq 1). This preparative sequence can be carried out on a reasonably large scale (0.2 mol) and produces overall yields of about 50%. (1) Handling, Storage, and Precautions: when stored in a freezer under an atmosphere of argon the reagent is stable for extended periods of time (years). It should be distilled prior to use and handled only in a well-ventilated 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: Dataset · Consensus signal: none
Teacher disagreement score0.022
Threshold uncertainty score0.072

Distilled classifier scores by category (both heads)

CategoryCodexGemma
Metaresearch0.0000.000
Meta-epidemiology (narrow)0.0010.000
Meta-epidemiology (broad)0.0000.000
Bibliometrics0.0010.001
Science and technology studies0.0000.000
Scholarly communication0.0000.000
Open science0.0010.000
Research integrity0.0000.001
Insufficient payload (model declined to judge)0.0220.012

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 head0.018
GPT teacher head0.253
Teacher spread0.234 · 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
GenreDataset

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
Published2001
Admission routes1
Has abstractyes

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