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Record W2003769072 · doi:10.1139/v00-185

Synthesis, characterization and chemistry of bis-(pentafluorophenyl)boryl ferrocene

2001· article· en· W2003769072 on OpenAlexfundvenueno aff
Bryon Carpenter, Warren E. Piers, Masood Parvez, Glenn P. A. Yap, Steven J. Rettig

Bibliographic record

VenueCanadian Journal of Chemistry · 2001
Typearticle
Languageen
FieldChemistry
TopicOrganoboron and organosilicon chemistry
Canadian institutionsnot available
FundersNatural Sciences and Engineering Research Council of CanadaUniversity of Calgary
KeywordsChemistryFerroceneLewis acids and basesAdductBoronMedicinal chemistryTransmetalationAcetonitrileIntramolecular forceOxidizing agentBorylationCarboraneInorganic chemistryStereochemistryOrganic chemistryArylAlkylElectrochemistryCatalysisPhysical chemistry

Abstract

fetched live from OpenAlex

Bis-(pentafluorophenyl)boryl ferrocene, 1, was prepared via borylation of ferrocene with HB(C 6 F 5 ) 2 or via a transmetallation reaction involving FcHgCl and ClB(C 6 F 5 ) 2 in 87–91% yield. The compound is characterized by a deep maroon colour. A significant intramolecular iron–boron interaction is manifested in the solution spectroscopic (Fe [Formula: see text] B charge transfer band at ~230 nm, ε = 1.33 × 10 4 ) and solid-state crystallographic data (Fe-B = 2.924 Å) This interaction has an impact on the Lewis acidity of the boron center which, unlike the related compound B(C 6 F 5 ) 3 , does not strongly bind Lewis bases such as acetone, THF, or acetonitrile. However, an adduct between the stronger base PMe 3 and 1 forms readily and this complex (2) was fully characterized. The electron withdrawing -B(C 6 F 5 ) 2 group causes 1 to be oxidized at +450 mV relative to ferrocene. Oxidation of 1 with [NO][BF 4 ], AgOSO 2 CF 3 , or AgC 6 F 5 leads to the zwitterionic ferrocenium borates 3-F, 3-OTf, and 3-C 6 F 5 , respectively. Each of these compounds was characterized spectroscopically and via X-ray crystallography. The properties of these compounds relative to 1 suggest that oxidation of the iron center significantly enhances the Lewis acidity of the boron center. Due to the σ-donating ability of the borate substituents, zwitterions 3 are weaker oxidizing agents than unsubstituted ferrocenium salts.Key words: organoboranes, ferrocene derivatives, Lewis acids.

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)0.000
Version: codex-gemma-dda1882f352aValidation status: machine_predicted_unvalidated
Candidate categoriesMeta-epidemiology (narrow), Insufficient payload (model declined to judge)
Consensus categoriesnone
DomainCandidate signal: none · Consensus signal: none
Study designCandidate signal: Bench or experimental · Consensus signal: Bench or experimental
GenreCandidate signal: Empirical · Consensus signal: Empirical
Teacher disagreement score0.014
Threshold uncertainty score1.000

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0000.000
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0010.000
Bibliometrics0.0000.000
Science and technology studies0.0000.000
Scholarly communication0.0000.000
Open science0.0000.000
Research integrity0.0000.000
Insufficient payload (model declined to judge)0.0110.000

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 head0.008
GPT teacher head0.194
Teacher spread0.186 · 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 designBench or experimental
Domainnot available
GenreEmpirical

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

Citations77
Published2001
Admission routes2
Has abstractyes

Explore more

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