Interrupted Carbonyl–Olefin Metathesis of Cyclic, Aliphatic Ketones
Bibliographic record
Abstract
Functionalized pentalenes, indenes, naphthalenes and azulenes represent common structural motifs in many compounds of biological importance. We herein describe an iron-catalyzed synthetic strategy that enables access to these central scaffolds in two steps from commercial material. This method complements established transformations between carbonyl and olefin moieties, such as carbonyl–ene, Prins and carbonyl–olefin metathesis (COM) reactions as a fourth reactivity mode. Experimental and theoretical investigations support a mechanism that interrupts the carbonyl–olefin metathesis reaction pathway through the distinct fragmentation of intermediate oxetanes resulting in the direct formation of functionalized pentalenes, indenes, naphthalenes, and azulenes. The scope of this iron-catalyzed transformation between carbonyl and olefin functionalities is demonstrated with 19 examples proceeding in up to 99% yield.
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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 | 0.001 |
| 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 | 0.001 | 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".