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Record W2049748813 · doi:10.1021/om0110888

Deactivation of Ruthenium Metathesis Catalysts via Facile Formation of Face-Bridged Dimers

2002· article· en· W2049748813 on OpenAlexaff
Dino Amoroso, Glenn P. A. Yap, Deryn E. Fogg

Bibliographic record

VenueOrganometallics · 2002
Typearticle
Languageen
FieldChemistry
TopicSynthetic Organic Chemistry Methods
Canadian institutionsUniversity of Ottawa
Fundersnot available
KeywordsChemistryCarbeneMetathesisCatalysisIsopreneNorborneneRutheniumLigand (biochemistry)Medicinal chemistryDerivative (finance)Salt metathesis reactionStereochemistryPolymerizationOrganic chemistryCopolymer

Abstract

fetched live from OpenAlex

Reaction of RuCl(dcypb)(μ-Cl) 3 Ru(dcypb)(N 2 ) ( 3 ) with an excess of tert -butylacetylene at ambient temperatures yields the dinuclear monovinylidene RuCl(dcypb)(μ-Cl) 3 Ru(dcypb)(L) ( 4a; L = C CHBu t, dcypb = 1,4-bis(dicyclohexylphosphino)butane), rather than the expected mononuclear RuCl 2 (dcypb)(L). Attempted synthesis of an allenylidene derivative via the corresponding reaction with 1,1-diphenyl-2-propyn-1-ol stops at the stage of hydroxyvinylidene 4b (L = C CHC(OH)Ph 2 ). While formation of these dinuclear products may be an artifact of low solubility, the corresponding monoalkylidene species 4c (L = CHCH CMe 2 ) is obtained on treating soluble RuH(dcypb)(μ-Cl) 2 (μ-H)Ru(dcypb)(H 2 ) ( 5 ) with 3-methyl-3-chloro-1-butyne. Formation of the perchloro species 4c is consistent with facile homodimerization of the initially formed RuCl 2 (dcypb)(CHCH CMe 2 ) ( 2d ), with expulsion of one alkylidene ligand as the free carbene. 2,7-Dimethylocta-2,4,6-triene, the formal product of carbene coupling, is observed by 1 H NMR. A minor product in this synthesis is proposed to be RuCl(dcypb)(μ-Cl) 2 (μ 2,η 1 -CHCH CMe 2 )RuCl(dcypb) ( 8 ). While the low activity of 4a / 4b in ring-opening metathesis polymerization of norbornene is attributable to their low solubility, that of 4c points toward the stability of the Ru 2 (μ-Cl) 3 entity. The low activity and facile formation of 4c reveals an important deactivation pathway for catalysts of type 2d, with additional relevance to other such chlororuthenium complexes, including systems of the Grubbs type. Product identities were established by 1 H, 2 H, 13 C, and 31 P NMR and IR spectroscopy and (for 4c and 5 ) by 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 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: Empirical · Consensus signal: Empirical
Teacher disagreement score0.002
Threshold uncertainty score0.006

Distilled classifier scores by category (both heads)

CategoryCodexGemma
Metaresearch0.0000.000
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 integrity0.0000.001
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 head0.030
GPT teacher head0.230
Teacher spread0.201 · 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
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

Citations62
Published2002
Admission routes1
Has abstractyes

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