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Record W4407751282 · doi:10.1021/acs.joc.4c02083

The Mechanism of the Cycloaddition of Substituted Ketenes to Cyclopentadiene Based on the Bent Bond/Antiperiplanar Hypothesis Orbital Model

2025· article· en· W4407751282 on OpenAlexafffund
Mathis Lefebvre, Paul A. Johnson, Pierre Deslongchamps

Bibliographic record

VenueThe Journal of Organic Chemistry · 2025
Typearticle
Languageen
FieldChemistry
TopicOrganic Chemistry Cycloaddition Reactions
Canadian institutionsUniversité Laval
FundersNatural Sciences and Engineering Research Council of Canada
KeywordsCyclopentadieneCycloadditionBent molecular geometryAlkane stereochemistryChemistryBicyclic moleculeRing (chemistry)StereochemistryComputational chemistryCrystallographyCrystal structureOrganic chemistryCatalysis

Abstract

fetched live from OpenAlex

The [2 + 2] cycloaddition of substituted ketenes with cyclopentadiene producing bicyclo[3.2.0]hept-2-en-6-ones is rationalized by the Bent Bond/Antiperiplanar Hypothesis (BBAH) orbital model. With monosubstituted ketenes, the endo isomer is formed preferentially. The endo and exo isomers are both produced with the cyclobutanone ring in the co-folded in conformation. Computational results support the analysis of the BBAH based mechanism in agreement with experimental results.

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)0.001
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 score0.019
Threshold uncertainty score0.999

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0010.001
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0000.000
Bibliometrics0.0000.001
Science and technology studies0.0010.000
Scholarly communication0.0000.000
Open science0.0020.000
Research integrity0.0000.001
Insufficient payload (model declined to judge)0.0020.000

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 head0.009
GPT teacher head0.203
Teacher spread0.195 · 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

Citations0
Published2025
Admission routes2
Has abstractyes

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