Accessible, Direct Photochemical Route for the Amine-Free Synthesis of Azoxybenzene and Functional Azoxy Derivatives via Nitroarene Homocoupling
Bibliographic record
Abstract
In this body of work, I report on a direct photochemical method for the one-pot synthesis of azoxybenzene and substituted azoxy derivatives from nitrobenzene building blocks. Using this approach, a 100% conversion efficiency of nitrobenzene and 93% yield of azoxybenzene was achieved. This protocol can be replicated at room temperature and under air, without the assistance of additional catalysts or reagents, and can be applied to substrates with a wide range of substituent groups. A family of porphyrin silane compounds were also studied as potential photocatalysts to facilitate the reduction of nitrobenzene to aniline. Although a 90% conversion efficiency of nitrobenzene and 32% yield of aniline was achieved, observed degradation of the catalysts limit potential application of this system.
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How this classification was reachedexpand
Full frame machine prediction
Teacher imitationNot calibrated prevalence, not ground truth. Human validation pending. The Gemma side is a direct model label for every work in the frame, read from the title-only record. The Codex side is a classifier learned from the 10,348 direct Codex labels and calibrated to design-weighted sample rates; fields without enough sample support carry no Codex call. Candidate is the union of the two sides; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels.
Distilled classifier scores by category (both heads)
| Category | Codex | Gemma |
|---|---|---|
| Metaresearch | 0.000 | 0.000 |
| 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 | 0.000 | 0.000 |
| Research integrity | 0.000 | 0.001 |
| Insufficient payload (model declined to judge) | 0.002 | 0.001 |
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 source (direct Gemma or distilled Codex), 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".