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Record W1915443664 · doi:10.1021/acs.organomet.5b00546

Diverging Pathways in the Activation of Allenes with Lewis Acids and Bases: Addition, 1,2-Carboboration, and Cyclization

2015· article· en· W1915443664 on OpenAlexafffund
Rebecca L. Melen, Lewis C. Wilkins, Benson M. Kariuki, Hubert Wadepohl, Lutz H. Gade, A. Stephen K. Hashmi, Douglas W. Stephan, Max M. Hansmann

Bibliographic record

VenueOrganometallics · 2015
Typearticle
Languageen
FieldChemistry
TopicOrganoboron and organosilicon chemistry
Canadian institutionsUniversity of Toronto
FundersStudienstiftung des Deutschen VolkesCanada Research ChairsVerband der Chemischen Industrie
KeywordsAlleneChemistryLewis acids and basesNucleophileKetoneBase (topology)Frustrated Lewis pairMedicinal chemistryStereochemistryCatalysisOrganic chemistry

Abstract

fetched live from OpenAlex

High Resolution Image Download MS PowerPoint Slide The reactions of allenes with frustrated (or cooperative) Lewis acid/base pairs result in the 1,4-addition of the base pair to the allene. The reactions of allenyl ketones and esters just in the presence of the strong Lewis acid B(C 6 F 5 ) 3 afford the selective formation of the 1,2-carboboration products. In both cases the Lewis acid activates the allene to either a C 6 F 5 migration or nucleophilic attack by the Lewis base. In addition to the 1,2-carboboration pathway, which can be viewed as being triggered by activation of the ketone (σ-activation), in the case of allenyl esters the corresponding cyclization products are observed in the presence of water.

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 score0.178
Threshold uncertainty score0.449

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 head0.021
GPT teacher head0.211
Teacher spread0.191 · 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

Citations47
Published2015
Admission routes2
Has abstractyes

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