MétaCan
Menu
Back to cohort
Record W2043838519 · doi:10.1002/ejoc.200801025

Cesium (<i>Z</i>)‐2‐Carbomethoxyethenethiolate: A Reagent for the Preparation of (<i>Z</i>)‐2‐Carbomethoxyethenyl Thioethers Including Selected Cysteine and Homocysteine Derivatives

2008· article· en· W2043838519 on OpenAlexaff
Jennifer S. O’Donnell, Suneel P. Singh, Thomas A. Metcalf, Adrian L. Schwan

Bibliographic record

VenueEuropean Journal of Organic Chemistry · 2008
Typearticle
Languageen
FieldChemistry
TopicChemical Synthesis and Reactions
Canadian institutionsUniversity of Guelph
Fundersnot available
KeywordsChemistryReagentElectrophileCaesiumBase (topology)Substitution reactionAlkylElectrophilic substitutionEnantiomerConjugateCysteineMedicinal chemistryCombinatorial chemistryOrganic chemistryCatalysis

Abstract

fetched live from OpenAlex

Abstract As a means to circumvent the standard and sometimes troubling conjugate addition reaction of thiols to alkyl propiolates, a new reagent, cesium ( Z )‐2‐carbomethoxyethenethiolate, is introduced. The cesium carbonate mediated methanolysis of ( Z )‐2‐carbomethoxyethenyl thiolacetate at low temperature creates cesium ( Z )‐2‐carbomethoxyethenethiolate in solution. For base‐insensitive and solvolytically stable electrophiles, efficient substitution can be achieved by direct introduction to the electrophile. The conditions were adapted to accommodate base‐sensitive cysteine derivatives, and the use of DMF as a cosolvent permits the isolation of ( Z )‐2‐carbomethoxyethenyl cysteinyl thioethers in high enantiomeric purity (&gt;99:1 er ) and with good Z / E ratios. There was no evidence of carbon substitution reactions. (© Wiley‐VCH Verlag GmbH &amp; Co. KGaA, 69451 Weinheim, Germany, 2009)

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)0.001
metaresearch head score (Gemma)0.002
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 score0.005
Threshold uncertainty score0.871

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0010.002
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0010.000
Bibliometrics0.0000.000
Science and technology studies0.0000.000
Scholarly communication0.0000.000
Open science0.0010.000
Research integrity0.0000.001
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 head0.031
GPT teacher head0.263
Teacher spread0.232 · 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

Citations10
Published2008
Admission routes1
Has abstractyes

Explore more

Same venueEuropean Journal of Organic ChemistrySame topicChemical Synthesis and ReactionsFrench-language works237,207