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Record W2507303739 · doi:10.1002/ejoc.201600684

Complementary Methods for the Introduction of the (<i>E</i>)‐3‐(Pentafluorosulfanyl)allyl Chain unto O‐, N‐, S‐, and C‐Based Nucleophiles

2016· article· en· W2507303739 on OpenAlexafffund
Justine Desroches, Elsa Forcellini, Jean‐François Paquin

Bibliographic record

VenueEuropean Journal of Organic Chemistry · 2016
Typearticle
Languageen
FieldPharmacology, Toxicology and Pharmaceutics
TopicFluorine in Organic Chemistry
Canadian institutionsUniversité LavalPROTEO
FundersNatural Sciences and Engineering Research Council of CanadaFonds de recherche du Québec – Nature et technologiesUniversité Laval
KeywordsChemistryNucleophileMedicinal chemistryPhenolsOrganic chemistryRadical-nucleophilic aromatic substitutionCatalysisSubstitution reactionNucleophilic substitutionNucleophilic aromatic substitution

Abstract

fetched live from OpenAlex

Two methods for the introduction of the (E)‐3‐(pentafluorosulfanyl)allyl chain unto various nucleophiles were investigated: a palladium‐catalyzed Tsuji–Trost reaction of (E)‐ethyl [3‐(pentafluorosulfanyl)allyl]carbonate and a nucleophilic substitution reaction on (E)‐[3‐(pentafluorosulfanyl)allyl] 4‐methylbenzenesulfonate. Various nucleophiles were examined including phenols, aliphatic and aromatic amines, aliphatic and aromatic thiols and malonates. Overall, the two approaches were found to be complementary as the Tsuji–Trost reaction worked better with phenols while the SN2 reaction generally provided better results with the amines. In addition, the sulfur‐based product could only be obtained using the SN2 reaction while the malonates only worked under the Tsuji–Trost conditions.

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: Bench or experimental · Consensus signal: Bench or experimental
GenreCandidate signal: Methods · Consensus signal: none
Teacher disagreement score0.002
Threshold uncertainty score0.007

Distilled classifier scores by category (both heads)

CategoryCodexGemma
Metaresearch0.0000.000
Meta-epidemiology (narrow)0.0010.000
Meta-epidemiology (broad)0.0000.000
Bibliometrics0.0000.000
Science and technology studies0.0000.000
Scholarly communication0.0000.000
Open science0.0000.000
Research integrity0.0010.001
Insufficient payload (model declined to judge)0.0020.001

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 head0.059
GPT teacher head0.392
Teacher spread0.332 · 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 designBench or experimental
Domainnot available
GenreMethods

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

Citations9
Published2016
Admission routes2
Has abstractyes

Explore more

Same venueEuropean Journal of Organic ChemistrySame topicFluorine in Organic ChemistryFrench-language works237,207