<i>N</i>‐Sulfanylimides as the Sulfur Source for Alkyl Allenyl Sulfoxides via [2,3]‐Sigmatropic Rearrangement
Bibliographic record
Abstract
Abstract Sulfenyl chlorides are a reliable starting material to access allenyl sulfoxides with aryl or haloalkyl groups by way of sulfenate ester formation followed by [2,3]‐sigmatropic rearrangement. Application of the chemistry of alkanesulfenyl chlorides is much less common due to competing fates along the reaction pathway. In this paper, N ‐sulfanylsuccimides (thiosuccinimides) are shown to be a viable replacement for sulfenyl chlorides. A number of allenyl alkyl sulfoxides are prepared in fair to good yields (21–73 %, 21 examples). In addition, some butyn‐1,4‐diols can be selectively monofunctionalized to form allenyl sulfoxides (26–71 %) with a hydroxyalkyl group geminal to the sulfur. Butynediols also permit synthetic access to dienes via successive sulfenate ester formation and [2,3]‐sigmatropic rearrangement reactions. N ‐2‐Trimethylsilylethylthosucinimides were among the highest yielding of the thioimides.
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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 | 0.001 |
| Meta-epidemiology (narrow) | 0.001 | 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 | 0.000 |
| 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 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".