The fragmentation of 7-norbornyloxychlorocarbene S<sub>N</sub>i-like transition states
Bibliographic record
Abstract
7-Norbornyloxychlorocarbene (15) fragments mainly to 7-norbornyl chloride (16). A C-2 deuterated analog of 15 (syn-15-d) fragments to labeled chloride 16 with 78% retention and 22% inversion. When the deuterium label is replaced by a syn-exo-2-methyl group, the resultant carbene 22 fragments to syn- and anti-7-chloro-exo-2-methylnorbornane in a ratio of 1:1.1, corresponding to 48% retention and 52% inversion. Computational studies suggest that the fragmentations proceed via competitive S N i-like transition states that lead to either retention or inversion. Key words: carbenes, carbocations, S N i reactions, stereochemistry.
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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 | 0.000 |
| 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) | 0.000 | 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".