Metathesis of P=C Bonds Catalyzed by N‐Heterocyclic Carbenes
Bibliographic record
Abstract
Abstract The catalytic metathesis of C=C bonds is a textbook reaction that has no parallel in the widely studied area of multiple bonds involving heavier p‐block elements. A high‐yielding P=C bond metathesis of phosphaalkenes (ArP=CPh 2 , Ar=Mes, o ‐Tol, Ph) has been discovered that is catalyzed by N‐heterocyclic carbenes (NHC=Me 2 IMe, Me 2 I i Pr). The products are cyclic oligomers formally derived from ArP=PAr [i. e. cyclo ‐(ArP) n ; n =3, 4, 5, 6] and Ph 2 C=CPh 2 . Preliminary mechanistic studies of this remarkable transformation have established NHC=PAr (Ar=Mes, o ‐Tol, Ph) as key phosphinidene transfer agents. In addition, novel cyclic intermediates, such as, cyclo ‐(ArP) 2 CPh 2 and cyclo ‐(ArP) 4 CPh 2 have also been observed. This work represents a rare application of non‐metal‐based catalysts for transformations involving main‐group elements.
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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 | 0.001 |
| Meta-epidemiology (narrow) | 0.000 | 0.000 |
| Meta-epidemiology (broad) | 0.001 | 0.000 |
| Bibliometrics | 0.000 | 0.000 |
| Science and technology studies | 0.000 | 0.000 |
| Scholarly communication | 0.000 | 0.000 |
| Open science | 0.001 | 0.000 |
| Research integrity | 0.000 | 0.001 |
| Insufficient payload (model declined to judge) | 0.012 | 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".