A one-pot method for the synthesis of 3-(hetero-)aryl-1,4,2-dioxazol-5-ones
Bibliographic record
Abstract
3-R-1,4,2-dioxazol-5-ones are a class of compounds that are increasingly finding diverse uses, including as regioselective amidation reagents and as electrolyte additives that enable long cycling lifetimes in rechargeable lithium-ion batteries. Conventional methods for their synthesis tend to be slow and time-consuming, requiring isolation and thorough drying of a hydroxamic acid intermediate, followed by a separate cyclization step with N,N′-carbonyldiimidazole. Furthermore, the cyclization is typically performed in dichloromethane, an environmentally harmful solvent. This work demonstrates a new one-pot method for the synthesis of these compounds that eliminates the need for isolation of the intermediate or the use of halogenated solvents. The reaction is mainly performed using environmentally benign ethyl acetate and a relatively small amount of N,N-dimethylformamide. The reaction proceeds readily at room temperature and requires no expensive metal catalysts to function.
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How this classification was reachedexpand
Full frame distilled prediction
Teacher imitationNot 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.
Codex and Gemma teacher scores by category
| Category | Codex | Gemma |
|---|---|---|
| Metaresearch | 0.000 | 0.002 |
| Meta-epidemiology (narrow) | 0.000 | 0.000 |
| Meta-epidemiology (broad) | 0.000 | 0.000 |
| Bibliometrics | 0.000 | 0.000 |
| Science and technology studies | 0.000 | 0.000 |
| Scholarly communication | 0.000 | 0.000 |
| Open science | 0.001 | 0.000 |
| Research integrity | 0.000 | 0.000 |
| Insufficient payload (model declined to judge) | 0.002 | 0.000 |
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.
score_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from itClassification
machine, unvalidatedMachine predicted; a candidate call from one teacher head, not a consensus.
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".