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Record W2134286205 · doi:10.1002/ejoc.200600836

Ruthenium(II)‐Catalyzed Cyclization of Oxabenzonorbornenes with Propargylic Alcohols: Formation of Isochromenes

2006· article· en· W2134286205 on OpenAlexafffund
Karine Villeneuve, William Tam

Bibliographic record

VenueEuropean Journal of Organic Chemistry · 2006
Typearticle
Languageen
FieldChemistry
TopicCatalytic Alkyne Reactions
Canadian institutionsUniversity of Guelph
FundersNatural Sciences and Engineering Research Council of Canada
KeywordsRutheniumChemistryCatalysisMethanolCarbeneAlkoxideCatalytic cycleTautomerMedicinal chemistryHydrideAlcoholPhotochemistryOrganic chemistryHydrogen

Abstract

fetched live from OpenAlex

Abstract The ruthenium‐catalyzed cyclization of a propargylic alcohol with an oxabenzonorbornene in methanol leads to an unanticipated isochromene framework. The catalytic cycle to form this product is believed to go through an oxidative cyclization of the two unsaturated partners with the ruthenium catalyst, followed by β‐hydride elimination, tautomerization andhydroruthenation. The ruthenacyclobutane thus obtained further undergoes [2+2] cycloreversion to form a ruthenium–carbene intermediate that atypically rearranges via a [1,3]‐alkoxide shift and finally reductively eliminates to produce the desired compound. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

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 score0.003
Threshold uncertainty score0.011

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 integrity0.0000.000
Insufficient payload (model declined to judge)0.0030.001

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 head0.007
GPT teacher head0.191
Teacher spread0.184 · 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

Citations35
Published2006
Admission routes2
Has abstractyes

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