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Record W4233945915 · doi:10.1002/047084289x.rd067

Di-<i>t</i>-butyl Peroxyoxalate

2001· reference-entry· he· W4233945915 on OpenAlexaff
John Boukouvalas

Bibliographic record

VenueEncyclopedia of Reagents for Organic Synthesis · 2001
Typereference-entry
Languagehe
FieldMaterials Science
TopicLanthanide and Transition Metal Complexes
Canadian institutionsUniversité Laval
Fundersnot available
KeywordsChemistryPentaneReagentSolventAnhydrousSolubilityOrganic chemistryPhotochemistry

Abstract

fetched live from OpenAlex

[1876-22-8] C10H18O6 (MW 234.25) (useful for clean, low-temperature generation of t-butoxyl radicals;1 induces cyclization of alkenyl hydroperoxides;2 used in radical-trapping experiments,3 and as initiator for alkene autoxidation4 and polymerization5) Alternate Name: DBPO. Physical Data: white crystals, mp 50.5–51.5 °C (dec).1a Solubility: sol most organic solvents (e.g. CH2Cl2, CCl4, PhH, PhCl, and pentane). Analysis of Reagent Purity: NMR (C6D6, δ) 1H: 1.12 (s), 13C: 25.7, 85.4 (no signal is observed for the carbonyl carbon);6 iodometric titration.1a Preparative Methods: readily obtained by reaction of Oxalyl Chloride with t-butyl hydroperoxide and pyridine in anhydrous pentane.1a,7 It is recommended to collect the crystals of DBPO on a precooled filter (−78 °C). Handling, Storage, and Precautions: the preparation and manipulation of DBPO must be conducted behind a safety shield. Tongs, gloves, and safety masks should be used throughout every operation. DBPO is highly sensitive to scratching or shock especially when the crystals are dry.1a In one instance, a violent explosion occurred during the transfer of solvent-wetted, recrystallized DBPO from one glass vessel to another.4a,b Consistent with the risk of explosion, it is recommended to use the reagent as prepared. If it must be stored, it should be kept in a flask under Ar at −20 °C or below. Ethers should not be used as solvents since they are known to accelerate perester decomposition.1a For most applications, benzene is the best solvent. Chemists new to the manipulation of organic peroxides are urged to read the appropriate literature before commencing experimental work.8

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)0.001
Version: codex-gemma-dda1882f352aValidation status: machine_predicted_unvalidated
Candidate categoriesMeta-epidemiology (narrow), Insufficient payload (model declined to judge)
Consensus categoriesMeta-epidemiology (narrow), Insufficient payload (model declined to judge)
DomainCandidate signal: none · Consensus signal: none
Study designCandidate signal: Not applicable · Consensus signal: Not applicable
GenreCandidate signal: Empirical · Consensus signal: none
Teacher disagreement score0.383
Threshold uncertainty score1.000

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0010.001
Meta-epidemiology (narrow)0.0010.001
Meta-epidemiology (broad)0.0030.001
Bibliometrics0.0000.001
Science and technology studies0.0010.000
Scholarly communication0.0000.000
Open science0.0020.000
Research integrity0.0010.000
Insufficient payload (model declined to judge)0.0440.002

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 head0.025
GPT teacher head0.256
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; both teacher heads agree on what is shown here.

Study designNot applicable
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

Citations0
Published2001
Admission routes1
Has abstractyes

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