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Record W4413800840 · doi:10.1002/chem.202502138

Synthesis of Cyclobutenoates from Photochemical Rearrangement of α‐Diazo Cyclopropanes and Computational Studies

2025· article· en· W4413800840 on OpenAlexafffund
Raphaël Dollet, Claude Y. Legault, Thomas Poisson, Philippe Jubault

Bibliographic record

VenueChemistry - A European Journal · 2025
Typearticle
Languageen
FieldChemistry
TopicCyclopropane Reaction Mechanisms
Canadian institutionsUniversité de Sherbrooke
FundersAlliance de recherche numérique du CanadaRégion NormandieAgence Nationale de la RechercheNormandie UniversitéUniversité de RouenCentre National de la Recherche ScientifiqueIndian National Science Academy
KeywordsStructural isomerCarbeneDiazoSinglet stateChemistryRing (chemistry)Reaction mechanismComputational chemistryPhotochemistryCombinatorial chemistryStereochemistryMedicinal chemistryOrganic chemistryCatalysisExcited statePhysicsAtomic physics

Abstract

fetched live from OpenAlex

The ring expansion of α-cyclopropyl diazoacetates into cyclobutenoates upon irradiation at 425 nm was reported. This method allowed an access to a large array of cyclobutenoates as a mixture of regioisomers. The products were isolated in moderate to excellent yields (17% to 75%) and moderate to good regioisomeric ratio (55:45 to 82:18). The synthetic utility of the products was showcased and the mechanism was studied. Thanks to DFT calculations, the formation of two regioisomers was explained as well as the involvement of a singlet state carbene.

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)0.000
metaresearch head score (Gemma)0.000
Version: codex-gemma-dda1882f352aValidation 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 score0.011
Threshold uncertainty score0.852

Codex and Gemma teacher scores by category

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)0.0000.000

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 head0.253
Teacher spread0.237 · 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.

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

Citations1
Published2025
Admission routes2
Has abstractyes

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