Cascading Radical Cyclization of Bis-Vinyl Ethers: Mechanistic Investigation Reveals a 5-<i>exo</i>/3-<i>exo</i>/retro-3-<i>exo</i>/5-<i>exo</i> Pathway
Bibliographic record
Abstract
We recently described an iterative synthesis of oligo-vinyl\nethers, followed by a radical cascade to provide a family of hexahydro-2<i>H</i>-furo[3,4-<i>b</i>]pyrans. Our results for the\nradical cascade were consistent with either a direct 6-<i>endo</i>-<i>trig</i> addition of a vinyl radical onto the first\nvinyl ether function or an initial 5-<i>exo</i>-<i>trig</i> addition, followed by rearrangement to the more stable\nanomeric radical intermediate. In this report, we describe our further\nmechanistic studies aimed at distinguishing between these two possibilities\nand conclude that the 5-<i>exo</i>/3-<i>exo</i>/retro-3-<i>exo</i> pathway is dominant.
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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 | 0.004 | 0.037 |
| Meta-epidemiology (narrow) | 0.006 | 0.006 |
| Meta-epidemiology (broad) | 0.006 | 0.004 |
| Bibliometrics | 0.003 | 0.006 |
| Science and technology studies | 0.003 | 0.002 |
| Scholarly communication | 0.001 | 0.004 |
| Open science | 0.007 | 0.003 |
| Research integrity | 0.007 | 0.004 |
| Insufficient payload (model declined to judge) | 0.087 | 0.007 |
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; both teacher heads agree on what is shown here.
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".