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Record W4244348915 · doi:10.1002/047084289x.ri081m

Isopropyldiphenylsulfonium Tetrafluoroborate

2001· reference-entry· en· W4244348915 on OpenAlexaff
Tony Durst, Robert N. Ben

Bibliographic record

VenueEncyclopedia of Reagents for Organic Synthesis · 2001
Typereference-entry
Languageen
FieldChemistry
TopicCyclopropane Reaction Mechanisms
Canadian institutionsUniversity of Ottawa
Fundersnot available
KeywordsYlideTetrafluoroborateChemistrySulfoniumReagentSulfideIodideMedicinal chemistrySalt (chemistry)Organic chemistryPolymer chemistryIonic liquidCatalysis

Abstract

fetched live from OpenAlex

[1660-43-7] C15H17BF4S (MW 316.20) InChI = 1S/C15H17S.BF4/c1-13(2)16(14-9-5-3-6-10-14)15-11-7-4-8-12-15;2-1(3,4)5/h3-13H,1-2H3;/q+1;-1 InChIKey = OYVGOJMOYZVZFZ-UHFFFAOYSA-N (transformation of carbonyls to gem-dimethyloxiranes;2 conversion of α,β-unsaturated systems3 and diene esters4 to geminal substituted cyclopropanes) Preparative Method: this reagent is not commercially available and must be made prior to use. The ylide isopropylidenediphenylsulfurane, obtained by deprotonation with an appropriate base, is usually formed in situ and used immediately because of its extremely low stability.2 Two methods have been reported for the preparation of the sulfurane. Ethyldiphenylsulfonium tetrafluoroborate (formed by the reaction of diphenyl sulfide with triethyloxonium tetrafluoroborate, eq 1) is suspended in a solution of DME. The ylide is formed by addition of LiCHCl2 at −70 °C and reacted with MeI (1.1 equiv). The desired sulfonium salt precipitates from solution. The isopropylidenediphenylsulfurane is formed by addition of LDA to this suspension at −78 °C (eq 2).2 (1) (2) A second, but less efficient, method of preparation involves the reaction of diphenyl sulfide, AgBF4, and neat isopropyl iodide (eq 3).2 (3) Three different base/solvent systems have been used to generate the isopropylidenediphenylsulfurane ylide: DME/LiCHCl2, t-BuOK/THF,5 and PhLi/THF.6 All methods have proven equally efficient. Different diastereomer ratios have been obtained with the t-BuOK/THF method compared to the other systems.7

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)0.000
metaresearch head score (Gemma)0.001
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 score0.750
Threshold uncertainty score1.000

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0000.001
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)0.0270.001

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 head0.017
GPT teacher head0.244
Teacher spread0.227 · 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 teacher head, not a consensus.

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
Published2001
Admission routes1
Has abstractyes

Explore more

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