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Record W1880956194 · doi:10.1139/v01-016

Diaryloxycarbenes from oxadiazolines

2001· article· en· W1880956194 on OpenAlexvenueno aff
Xiaosong Lu, Darren L. Reid, John Warkentin

Bibliographic record

VenueCanadian Journal of Chemistry · 2001
Typearticle
Languageen
FieldChemistry
TopicCyclopropane Reaction Mechanisms
Canadian institutionsnot available
Fundersnot available
KeywordsKeteneChemistryDimethyl acetylenedicarboxylateTriethyl orthoformateBenzeneYlideAcetoneMedicinal chemistryPhenolThermal decompositionHydrazoneCyclohexanoneAcetalDecompositionOrganic chemistryCycloaddition

Abstract

fetched live from OpenAlex

Symmetric and unsymmetric 2,2-diaryloxy-5,5-dimethyl-Δ 3 -1,3,4-oxadiazolines were synthesized by oxidative cyclization of aryloxycarbonyl hydrazones of acetone with lead tetraacetate and subsequent treatment of the product mixture with a phenol in acidic solution. Thermolysis of the oxadiazolines in benzene solution at 110°C afforded carbonyl ylide intermediates that cyclize, in part, to the corresponding 2,2-diaryloxyoxirane intermediates. The oxiranes, which were not observed, are required to account for the 1,1-diaryloxy-2-methylpropenes (ketene acetals) that were isolated. Most of the carbonyl ylides fragment to acetone and diaryloxycarbenes. The latter form dimers (tetraaryloxyethenes) or they can be trapped with phenols to form orthoformates. Diphenoxycarbene was also trapped with dimethyl acetylenedicarboxylate (DMAD). The method appears to be the first for generating the parent diphenoxycarbene under relatively mild conditions in solution, and the only one to date for generating unsymmetrically substituted diaryloxycarbenes. Minor competing fragmentations of the oxadiazolines to 2-diazopropane and the appropriate diaryl carbonates, were also observed.Key words: diarylcarbonate, diaryloxycarbene, diaryloxy oxadiazoline, ketene acetal, orthoformate.

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 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 score0.163
Threshold uncertainty score0.991

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)0.0090.000

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 head0.010
GPT teacher head0.202
Teacher spread0.192 · 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.

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

Citations9
Published2001
Admission routes1
Has abstractyes

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