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Record W2317705787 · doi:10.1021/om501011y

Donor-Induced Decomposition of the Grubbs Catalysts: An Intercepted Intermediate

2014· article· en· W2317705787 on OpenAlex

Why this work is in the frame

A frame that forgets how it found something cannot be audited. These are the routes that admitted this work.

affAt least one author lists a Canadian institution in the pinned OpenAlex snapshot.
fundA Canadian funder is recorded on the work.

Bibliographic record

VenueOrganometallics · 2014
Typearticle
Languageen
FieldChemistry
TopicSynthetic Organic Chemistry Methods
Canadian institutionsUniversity of AlbertaUniversity of Ottawa
FundersNatural Sciences and Engineering Research Council of Canada
KeywordsChemistryPyridineNucleophileSteric effectsMetathesisAdductMedicinal chemistryLigand (biochemistry)CatalysisStereochemistryAlkylOrganic chemistryReceptor

Abstract

fetched live from OpenAlex

The σ-alkyl species RuCl 2 (CH 2 PCy 3 )(py) 3 ( 3a ) is intercepted on adding pyridine to the first-generation Grubbs catalyst 1a during RCM or to the isolated resting-state species RuCl 2 (PCy 3 ) 2 (═CH 2 ) ( 2a ). Complex 3a is formed by pyridine-induced displacement of PCy 3 and nucleophilic attack of the liberated PCy 3 on the methylidene carbon. The rapid, near-quantitative conversion of 2a into 3a indicates that nucleophilic attack by PCy 3 is the primary deactivating event. Once formed, 3a decomposes more slowly via several competing pathways. One such pathway involves elimination of the σ-alkyl ligand as [CH 3 PCy 3 ]Cl ( A ), following proton and chloride abstraction. Observation of nearly 80% 3a during RCM by 1a in the presence of pyridine confirms the relevance of this behavior to metathesis and implicates the resting-state methylidene 2a as the vulnerable species, rather than the metallacyclobutane intermediate. Any donor capable of displacing PCy 3 and stabilizing a five-coordinate methylidene adduct is predicted to trigger the same deactivation sequence, steric factors permitting.

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.

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 score0.013
Threshold uncertainty score0.998

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 science0.0010.000
Research integrity0.0000.000
Insufficient payload (model declined to judge)0.0030.000

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 head0.016
GPT teacher head0.278
Teacher spread0.262 · 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