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Record W4254882061 · doi:10.1002/047084289x.rn02021

<i>N,N,S</i>-Trimethyl-<i>S</i>-phenylsulfoxinium Tetrafluoroborate

2017· reference-entry· he· W4254882061 on OpenAlexaff
Pauline Rullière

Bibliographic record

VenueEncyclopedia of Reagents for Organic Synthesis · 2017
Typereference-entry
Languagehe
FieldChemistry
TopicSulfur-Based Synthesis Techniques
Canadian institutionsUniversité de Montréal
Fundersnot available
KeywordsTetrafluoroborateDichloromethaneChemistryReagentChloroformSolubilityYlideMedicinal chemistryTetrahydrofuranDimethyl sulfoxideOrganic chemistryNuclear chemistryIonic liquidSolventCatalysis

Abstract

fetched live from OpenAlex

[21077-81-6] C9H14BF4NOS (MW 271.08) InChI = 1S/C9H14NOS.BF4/c1-10(2)12(3,11)9-7-5-4-6-8-9;2-1(3,4)5/h4-8H,1-3H3;/q+1;-1 InChIKey = UWILSOUJFCSHMO-UHFFFAOYSA-N (sulfoximine salt; ylide precursor; cyclopropanating reagent) Alternative Names: (dimethylamino)methylphenylsulfoxonium tetrafluoroborate. Physical Data: white solid, mp 118–119 °C. Solubility: soluble in dimethylformamide, dimethylsulfoxide, dichloromethane, tetrahydrofuran (low solubility), chloroform. Preparative Methods: synthesized from commercially available methyl phenyl sulfoxide or S-methyl S-phenyl sulfoximine. The methyl phenyl sulfoxide is converted to the sulfoximine with hydrazoic acid (1.1 equiv). Alkylation of free sulfoximine to (dimethylamino)oxosulfonium tetrafluoroborate is then accomplished in 80% yield using 2.5 equiv of trimethyloxonium tetrafluoroborate (eq 1).1-3 Analysis of Reagent: 1H NMR (500 MHz, CDCl3) δ 7.83–8.27 (m, 5H), 4.03 (s, 3H), 3.16 (s, 6H). IR ν 1100–1000 cm−1. Handling, Storage, and Precautions: not specified but the corresponding ylide 2 has shown long-term stability, as it could be stored for 2 months in solution in DMSO-d6 at room temperature without any sign of degradation.2

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)0.003
metaresearch head score (Gemma)0.021
Version: codex-gemma-dda1882f352aValidation status: machine_predicted_unvalidated
Candidate categoriesMetaresearch, Meta-epidemiology (narrow), Open science, 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: none
GenreCandidate signal: Other · Consensus signal: none
Teacher disagreement score0.500
Threshold uncertainty score1.000

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0030.021
Meta-epidemiology (narrow)0.0040.004
Meta-epidemiology (broad)0.0060.003
Bibliometrics0.0010.001
Science and technology studies0.0010.001
Scholarly communication0.0000.001
Open science0.0080.001
Research integrity0.0050.002
Insufficient payload (model declined to judge)0.0220.001

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 head0.282
Teacher spread0.256 · 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".

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Citations0
Published2017
Admission routes1
Has abstractyes

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