Amine‐Mediated Degradation in Olefin Metathesis Reactions that Employ the Second‐Generation Grubbs Catalyst
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Bibliographic record
Abstract
Abstract Amine‐mediated decomposition during olefin metathesis reactions that employ the second‐generation Grubbs catalyst is studied. For most amines, the dominant deactivation pathway involves ejection of the PCy 3 (Cy=cyclohexyl) ligand by the amine, followed by abstraction of the methylidene moiety from the resting‐state species RuCl 2 (H 2 IMes)(PCy 3 )(=CH 2 ) (H 2 IMes=1,3‐dimesityl‐4,5‐dihydroimidazol‐2‐ylidene) as [MePCy 3 ]Cl. An exception is highly basic 1,8‐diazabicyclo[5.4.0]undec‐7‐ene (DBU), which is slow to degrade the resting‐state methylidene complex, and for which the phosphonium byproduct is not observed. However, DBU is shown to rapidly attack a species generated during catalysis, most probably the metallacyclobutane intermediate.
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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 | 0.002 |
| 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 | 0.000 |
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 it