Construction of Isochromenes via a Ruthenium-Catalyzed Reaction of Oxabenzonorbornenes with Propargylic Alcohols
Bibliographic record
Abstract
The ruthenium-catalyzed cyclization of a propargylic alcohol with an oxabenzonorbornene in methanol leads to the creation of an isochromene framework. The proposed mechanism herein discussed for the formation of the product involves six major steps, the first four being oxidative cyclization, β-hydride elimination, hydroruthenation, followed by [2+2] cycloreversion. The ruthenium carbene formed at this stage undergoes a [1,3]-alkoxide shift that provides the observed product after reductive elimination. This process, believed to occur via a cationic ruthenium species, is in competition with two other pathways, ruthenium-catalyzed [2+2] cycloaddition and cyclopropanation. Although both [Cp*Ru(CH 3 CN) 3 ]PF 6 and Cp*Ru(COD)Cl are effective catalysts, the latter gives better yield and product ratio. The reaction was also found to proceed with high regioselectivity and product selectivity when unsymmetrical alkenes bearing a coordinating functional group at the bridge junction were used.
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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 | 0.001 | 0.000 |
| Meta-epidemiology (narrow) | 0.000 | 0.000 |
| Meta-epidemiology (broad) | 0.001 | 0.000 |
| Bibliometrics | 0.000 | 0.001 |
| Science and technology studies | 0.000 | 0.000 |
| Scholarly communication | 0.000 | 0.000 |
| Open science | 0.000 | 0.000 |
| Research integrity | 0.000 | 0.000 |
| 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".