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Record W2159078962 · doi:10.1002/ejoc.201403618

Interception of Nazarov Reactions of Allenyl Vinyl Ketones with Dienes: (3+2)‐ versus (4+3)‐Cycloaddition and Subsequent Rearrangement

2015· article· en· W2159078962 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

VenueEuropean Journal of Organic Chemistry · 2015
Typearticle
Languageen
FieldChemistry
TopicOrganic Chemistry Cycloaddition Reactions
Canadian institutionsDalhousie University
FundersNatural Sciences and Engineering Research Council of Canada
KeywordsCycloadditionChemistrySteric effectsRing (chemistry)DieneMedicinal chemistryMoleculeDecompositionTransition stateStereochemistryOrganic chemistryCatalysis

Abstract

fetched live from OpenAlex

Abstract Capture of the cyclic oxyallyl cation intermediates from the BF 3 ‐mediated Nazarov reactions of three allenyl vinyl ketones with various dienes was accomplished by (3+2)‐ and (4+3)‐cycloaddition. The relative amounts of these types of products were dependent on the substitution on the diene, and this could be linked to steric hindrance. Treatment of the (3+2)‐cycloaddition products with BF 3 · Et 2 O led mainly to decomposition but also to ring‐opened molecules and ring‐enlarged structures. The computed Gibbs energies of the (3+2)‐cycloaddition products, the products of the acid treatment and of some transition states leading to rearranged products were compared.

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)0.000
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 score0.020
Threshold uncertainty score0.998

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)0.0030.000

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 head0.025
GPT teacher head0.229
Teacher spread0.204 · 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