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Record W1949260568 · doi:10.1002/047084289x.rd374

Dimethyl Sulfoxide-Acetic Anhydride

2001· reference-entry· en· W1949260568 on OpenAlexaff
Thomas T. Tidwell

Bibliographic record

VenueEncyclopedia of Reagents for Organic Synthesis · 2001
Typereference-entry
Languageen
FieldChemistry
TopicAsymmetric Hydrogenation and Catalysis
Canadian institutionsUniversity of Toronto
Fundersnot available
KeywordsChemistryReagentAcetoneDimethyl sulfoxideAcetic anhydrideOrganic chemistryAlcoholAnhydrousIsopropyl alcoholSolubilityCatalysis

Abstract

fetched live from OpenAlex

(DMSO) [67-68-5] C2H6OS (MW 78.13) InChI = 1S/C2H6OS/c1-4(2)3/h1-2H3 InChIKey = IAZDPXIOMUYVGZ-UHFFFAOYSA-N (Ac2O) [108-24-7] C4H6O3 (MW 102.09) InChI = 1S/C4H6O3/c1-3(5)7-4(2)6/h1-2H3 InChIKey = WFDIJRYMOXRFFG-UHFFFAOYSA-N (oxidant for the conversion of primary and secondary alcohols to aldehydes and ketones, respectively; avoids overoxidation to carboxylic acids; suitable for large-scale oxidation; gives good yields with variable amounts of byproduct methylthiomethyl ethers) Alternate Name: Albright–Goldman reagent. Physical Data: DMSO mp 18.4 °C; bp 189 °C; d 1.101 g cm−3. Ac2O: mp −78 °C; bp 138–140 °C; d 1.082 g cm−3. Solubility: DMSO: sol H2O, alcohol, acetone, THF, CH2Cl2. Ac2O: sol ether, acetone, CH2Cl2. Form Supplied in: colorless liquids; widely available, including ‘anhydrous’ grades of DMSO packed under N2. Preparative Method: the active reagent, presumably Me2S+OAc, forms slowly from a mixture of the coreactants over a period of hours at rt and reacts with the alcohol in situ. Purification: DMSO: distillation from calcium hydride at 56–57 °C/5 mmHg2a or 83–85 °C/17 mmHg;2b storage over 3Å molecular sieves. Ac2O: distillation from aluminum chloride or calcium carbide. Handling, Storage, and Precautions: Dimethyl Sulfoxide is readily absorbed through the skin and should always be handled with gloves in a fume hood; its reactions form foul-smelling byproducts and should be carried out with good ventilation, and the waste byproducts and liquids used for washing should be treated with KMnO4 solution to oxidize volatile sulfur compounds; DMSO undergoes appreciable disproportionation to dimethyl sulfide (stench) and dimethyl sulfone above 90 °C;2c Acetic Anhydride is a corrosive lachrymator.

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)0.004
Version: codex-gemma-dda1882f352aValidation status: machine_predicted_unvalidated
Candidate categoriesMeta-epidemiology (narrow), Insufficient payload (model declined to judge)
Consensus categoriesnone
DomainCandidate signal: none · Consensus signal: none
Study designCandidate signal: Not applicable · Consensus signal: none
GenreCandidate signal: Other · Consensus signal: Other
Teacher disagreement score0.640
Threshold uncertainty score0.999

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0000.004
Meta-epidemiology (narrow)0.0010.001
Meta-epidemiology (broad)0.0020.001
Bibliometrics0.0010.001
Science and technology studies0.0000.000
Scholarly communication0.0000.000
Open science0.0010.000
Research integrity0.0010.000
Insufficient payload (model declined to judge)0.0270.000

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 head0.014
GPT teacher head0.247
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.

Study designNot applicable
Domainnot available
GenreOther

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

Explore more

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