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Record W2624469807 · doi:10.1021/acs.organomet.7b00034

Multiple C–H Activations of Linear Alkanes by Various (η<sup>5</sup>-Cyclopentadienyl)W(NO)(CH<sub>2</sub>CMe<sub>3</sub>)<sub>2</sub> Complexes

2017· article· en· W2624469807 on OpenAlexafffund
M.V. Shree, Diana Fabulyak, Rhett A. Baillie, Guillaume Lefèvre, Kevan E. Dettelbach, Aurélien Béthegnies, Brian O. Patrick, Peter Legzdins, Devon C. Rosenfeld

Bibliographic record

VenueOrganometallics · 2017
Typearticle
Languageen
FieldChemical Engineering
TopicCarbon dioxide utilization in catalysis
Canadian institutionsUniversity of British Columbia
FundersNatural Sciences and Engineering Research Council of CanadaWestern Canada Research GridDow Chemical Company
KeywordsChemistryCyclopentadienyl complexLigand (biochemistry)Steric effectsAlkaneAlkylMedicinal chemistrySubstituentThermal decompositionStereochemistryAcceptorHydrocarbonOrganic chemistryCatalysis

Abstract

fetched live from OpenAlex

As illustrated in the accompanying diagram, thermolysis of Cp*W(NO)(CH 2 CMe 3 ) 2 (Cp* = η 5 -C 5 Me 5 ) at 80 °C in neat linear alkanes effects three successive C–H bond activations of the hydrocarbon substrates and forms Cp*W(NO)(H)(η 3 -allyl) complexes in which the allyl ligands are derived from the alkanes. These allyl hydrido compounds exist in solutions as mixtures of isomers containing monosubstituted (i.e., terminal) or 1,3-disubstituted (i.e., internal) allyl ligands which can have either an endo or exo orientation with the substituent groups being either proximal or distal to the nitrosyl ligand. Due to steric factors the most abundant isomer in all cases has a monosubstituted allyl ligand in the endo orientation with the alkyl end distal to the nitrosyl ligand. In addition, the relative abundance of Cp*W(NO)(H)(η 3 -allyl) isomers having monosubstituted allyl ligands decreases with increasing length of the n -alkane chain. Further thermolysis of the Cp*W(NO)(H)(η 3 -allyl) complexes results in the liberation of alkenes. Whether initiated by Cp*W(NO)(CH 2 CMe 3 ) 2 or independently synthesized Cp*W(NO)(H)(η 3 -allyl) complexes, the n -alkane dehydrogenations generally result in the preferential formation of 1-alkenes. They are stoichiometric, and their outcomes are not significantly affected by varying the experimental conditions employed (e.g., time, temperature, an open system, use of an H 2 acceptor, etc.) or by changing the initial bis(neopentyl) tungsten reactant to its Cp Et (η 5 -C 5 Me 4 Et) and Cp i Pr (η 5 -C 5 H 4 i Pr) analogues or to Cp*Mo(NO)(CH 2 CMe 3 ) 2 . The results of DFT calculations are consistent with these dehydrogenations proceeding via 16e Cp*M(NO)(η 2 -alkene) (M = Mo, W) intermediates that are in equilibrium with their more stable 18e Cp*M(NO)(H)(η 3 -allyl) isomers. These intermediates facilitate the allyl ligand exchange reactions depicted in the accompanying diagram by functioning as internal hydrogen acceptors during the dehydrogenation of the linear alkanes. Thermolysis of the final hydrido allyl complexes liberates the desired alkenes.

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)0.001
metaresearch head score (Gemma)0.003
Version: codex-gemma-dda1882f352aValidation status: machine_predicted_unvalidated
Candidate categoriesMeta-epidemiology (narrow)
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 score0.037
Threshold uncertainty score0.999

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0010.003
Meta-epidemiology (narrow)0.0010.001
Meta-epidemiology (broad)0.0020.001
Bibliometrics0.0010.001
Science and technology studies0.0010.001
Scholarly communication0.0000.001
Open science0.0020.001
Research integrity0.0010.001
Insufficient payload (model declined to judge)0.0000.001

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 head0.014
GPT teacher head0.230
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

Citations6
Published2017
Admission routes2
Has abstractyes

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