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 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 | 0.000 |
| 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".