Iodosulfonation of alkenes with benzenesulfinic acid <i>N</i>-iodosuccinimide Facile preparation of α,β-unsaturated sulfones
Bibliographic record
Abstract
Reaction of alkenes and alkenols with N-iodosuccinimide (NIS) and benzenesulfinic acid in dichloromethane at room temperature affords vic-iodophenylsulfonyl adducts in good to high yields. Treatment of the iodosulfones with neutral alumina in dichloromethane at room temperature results in dehydroiodination to give the corresponding vinyl sulfones in high yield and purity by this convenient two-step procedure. Application of the iodosulfonationdehydroiodination sequence to allylic alcohols and silyl ethers gave γ-oxygenated, α,β-unsaturated phenylsulfones, while the attempted iodosulfonation of glycals, as intermediates to vinyl sulfones, resulted in addition of benzenesulfinic acid with double bond shift (Ferrier rearrangement). Key words: iodosulfonation, vinyl sulfones, benzenesulfinic acid, N-iodosuccinimide, dehydroiodination.
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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) | 0.001 | 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".