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Record W2001859185 · doi:10.1021/om030646a

Compatibility of the Vinylidene Ligand and Perfluorophenoxide

2004· article· en· W2001859185 on OpenAlexaff
Samantha D. Drouin, H.M. Foucault, Glenn P. A. Yap, Deryn E. Fogg

Bibliographic record

VenueOrganometallics · 2004
Typearticle
Languageen
FieldChemistry
TopicSynthetic Organic Chemistry Methods
Canadian institutionsUniversity of Ottawa
Fundersnot available
KeywordsChemistryDeprotonationDicationLigand (biochemistry)NucleophileMedicinal chemistryMoietyStereochemistryButaneAcetylideIonOrganic chemistry

Abstract

fetched live from OpenAlex

This study demonstrates the stability of the Ru-vinylidene moiety toward installation of a perfluorophenoxide ligand. The room-temperature reaction of RuCl(dcypb)(μ-Cl) 3 Ru(dcypb)(N 2 ) ( 3 ) with TlOC 6 F 5 and excess tert -butylacetylene yields mononuclear Ru(OC 6 F 5 ) 2 (dcypb)( C CHBu t ) ( 6, dcypb = 1,4-bis(dicyclohexylphosphino)butane). Intermediates en route to 6 are the face-bridged dimers RuCl(dcypb)(μ-Cl) 3 Ru(dcypb)( C CHBu t ) ( 4a ) and [{Ru(dcypb)( C CHBu t )} 2 (μ-Cl) 3 ]OC 6 F 5 ( 5 ·OC 6 F 5 ): the cation in the latter was characterized as its PF 6 salt (reaction halting at 5 ·PF 6 on use of TlPF 6 in place of TlOC 6 F 5 ). Edge-bridged, dicationic [{RuCl(dcypb)( C CHBu t )} 2 (μ-Cl) 2 ](OC 6 F 5 ) 2 ( 8 ) is also a probable intermediate in this reaction pathway: although not observed directly, the dication was isolated in low yields as its BAr f 4 salt, on reaction of 5 ·PF 6 with NaBAr f 4 (BAr f 4 - = [B{C 6 H 3 (CF 3 ) 2 -3,5} 4 ] - ). A minor byproduct in the synthesis of 6 is acetylide Tl[{Ru(C⋮CBu t )(dcypb)} 2 (μ-Cl) 3 ] ( 7 ), formed by deprotonation of the vinylidene ligand in 5 ·OC 6 F 5 by TlOC 6 F 5 . (An alternative representation of 7 as a covalent Ru(μ-Cl) 2 Tl species is supported by X-ray evidence, at least in the solid state.) Importantly, the deprotonation reaction is reversible, and competing reprotonation of 7 by the phenol coproduct enables re-formation of 5 ·OC 6 F 5 . Nucleophilic attack by the aryloxide anion on the metal center enables complete and irreversible transformation to 6, illustrating the mutual compatibility of the vinylidene and perfluorophenoxide ligands. As expected from the high thermodynamic stability of the Ru 2 (μ-Cl) 3 entity, complexes 5 ·PF 6 and 5 ·Cl exhibit low activity in ring-opening metathesis polymerization of norbornene. Mononuclear 6, containing four nonlabile ligands cis to the vinylidene moiety, is likewise quite unreactive until activated by protonolysis of aryloxide. Product identities were established by 1 H, 13 C, and 31 P NMR and IR spectroscopy, and ( 6, 7, 8 ) X-ray crystallography.

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 categoriesInsufficient 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 score0.005
Threshold uncertainty score1.000

Codex and Gemma teacher scores by category

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

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 head0.012
GPT teacher head0.229
Teacher spread0.217 · 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

Citations20
Published2004
Admission routes1
Has abstractyes

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