Direct Photochemical Route for Amine- and Catalyst-Free Synthesis of Azoxybenzene and Functional Azoxy Derivatives via Accessible Nitroarene Homocoupling under Ambient Conditions
Bibliographic record
Abstract
We report on a direct photochemical method for the one-pot, catalyst- and additive-free synthesis of azoxybenzene and substituted azoxy derivatives from nitrobenzene building blocks. This reaction is conducted at room temperature and under air, and can be applied to substrates with a wide range of substituents. Yields of products derived from para- and meta-substituted nitrobenzenes are typically good, while sterically encumbered ortho-substituted substrates are not as fruitful. Photochemical Wallach rearrangement of generated azoxybenzenes to ortho-hydroxyazoxybenzenes was observed in some cases, most markedly in selected ortho-halogenated nitrobenzenes. Overall, this method provides an efficient, green pathway to highly value-added azoxybenzene products.
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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 | 0.000 |
| Meta-epidemiology (narrow) | 0.000 | 0.000 |
| Meta-epidemiology (broad) | 0.001 | 0.000 |
| Bibliometrics | 0.000 | 0.000 |
| Science and technology studies | 0.000 | 0.000 |
| Scholarly communication | 0.000 | 0.000 |
| Open science | 0.000 | 0.001 |
| Research integrity | 0.000 | 0.001 |
| Insufficient payload (model declined to judge) | 0.001 | 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".