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Record W2952510649 · doi:10.1055/s-2001-10808

Conversion of Iodocyclopropanes into Cyclopropylzinc Chlorides and Pd(0)-Catalyzed Cross-Coupling of the Latter Derivatives with Alkenyl Iodides and Iodobenzene: Stereospecific Synthesis of 1,2-Bisalkenylcyclopropanes and 1-Alkenyl-2-phenylcyclopropanes

2001· article· en· W2952510649 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

VenueSynthesis · 2001
Typearticle
Languageen
FieldChemistry
TopicCyclopropane Reaction Mechanisms
Canadian institutionsUniversity of British Columbia
FundersNatural Sciences and Engineering Research Council of Canada
KeywordsChemistryTransmetalationIodobenzenePalladiumStereospecificityCatalysisMetalationMedicinal chemistryChlorideCoupling reactionZincOrganic chemistry

Abstract

fetched live from OpenAlex

A method for the preparation of functionalized cyclopropylzinc chlorides, which involves treatment of substituted 2-alkenyl-1-iodocyclopropanes with BuLi followed by transmetalation of the resultant cyclopropyllithium with zinc chloride, is described. Palladium(0)-catalyzed cross-coupling of the cyclopropylzinc chloride derivatives with alkenyl iodides or iodobenzene provides highly substituted 1,2-bisalkenylcyclopropanes or 1-alkenyl-2-phenylcyclopropanes. In two of the cases studied, the initially formed cis-1,2-bisalkenylcyclopropanes 27, 29 underwent partial Cope rearrangement under the cross-coupling conditions to afford the corresponding 1,4-cycloheptadienes 28 and 30, respectively.

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)0.001
metaresearch head score (Gemma)0.001
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 score0.185
Threshold uncertainty score1.000

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0010.001
Meta-epidemiology (narrow)0.0010.001
Meta-epidemiology (broad)0.0020.000
Bibliometrics0.0000.001
Science and technology studies0.0000.002
Scholarly communication0.0000.001
Open science0.0010.001
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 head0.009
GPT teacher head0.221
Teacher spread0.212 · 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