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Record W2949859869 · doi:10.1055/s-2000-6345

Allenylketenes: Versatile Substrates in Nucleophilic, Electrophilic, and Cycloaddition Reactions

2000· article· en· W2949859869 on OpenAlexafffund
Wenwei Huang, Thomas T. Tidwell

Bibliographic record

VenueSynthesis · 2000
Typearticle
Languageen
FieldChemistry
TopicOrganic Chemistry Cycloaddition Reactions
Canadian institutionsUniversity of Toronto
FundersNatural Sciences and Engineering Research Council of Canada
KeywordsChemistryElectrophileCycloadditionNucleophileTrimethylsilylMedicinal chemistryBenzaldehydeAnilineKeteneStereochemistryOrganic chemistryCatalysis

Abstract

fetched live from OpenAlex

All articles of this category 4-Methylene-2-trimethylsilyl-3-phenylcyclobutenones 3 are obtained from the corresponding cyclobutenedione 7 by Tebbe and Peterson methylenation reactions, and upon photolysis give 3-phenyl substituted allenylketenes R 1 CH=C=C(Ph)C(SiMe 3 )=C=O 4 . These are more reactive in ring closure back to 3 than are the 3-trimethylsilyl analogs 1 , as predicted on the basis of molecular orbital calculations. Reactions of allenylketenes 1 and 4 include addition of H 2 O followed by cyclization to form butenolides 13 , addition of aniline to give allenyl carboxamide 14 and lactam 15 , addition of CF 3 CO 2 H to form allenyl carboxylic acid 17 , addition of Br 2 in a 1,4-fashion to give penta-2,4-dienoic acid derivatives 18 , and reaction with m -chloroperbenzoic acid to give the unique allenyl acylsilane 23 . [4 + 1]-Cycloaddition reactions of 1 and 4 with Me 3 SiCHN 2 give methylenecyclopentenones 24 and 25 while acetaldehyde undergoes BF 3 · OEt 2 catalyzed [2 + 2] cycloadditions forming β-lactones. [4 + 2] Cycloadditions occur with benzaldehyde to form the highly crowded exomethylene pentenolactone 29 , and with TCNE forming methylenecyclohexenones 31 . allenes - ketenes - cyclobutenones - cycloaddition - silyl substituents - addition reactions - olefination reactions

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 machine prediction

Teacher imitation

Not calibrated prevalence, not ground truth. Human validation pending. The Gemma side is a direct model label for every work in the frame, read from the title-only record. The Codex side is a classifier learned from the 10,348 direct Codex labels and calibrated to design-weighted sample rates; fields without enough sample support carry no Codex call. Candidate is the union of the two sides; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels.

metaresearch head score (Codex)0.000
metaresearch head score (Gemma)0.000
Version: metacan-v3-hybrid-931329e0061cValidation 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 score0.002
Threshold uncertainty score0.005

Distilled classifier scores by category (both heads)

CategoryCodexGemma
Metaresearch0.0000.000
Meta-epidemiology (narrow)0.0010.000
Meta-epidemiology (broad)0.0000.000
Bibliometrics0.0000.000
Science and technology studies0.0000.000
Scholarly communication0.0000.001
Open science0.0000.000
Research integrity0.0000.001
Insufficient payload (model declined to judge)0.0020.001

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 head0.006
GPT teacher head0.196
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 source (direct Gemma or distilled Codex), 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

Citations19
Published2000
Admission routes2
Has abstractyes

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