A new fluorous soluble Lewis acidic borane system
Bibliographic record
Abstract
Treatment of trichlorovinylsilane with 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-1-octanol (3 equiv.) in the presence of excess triethylamine produces the fluorous vinylsilane, 1, which can be isolated in 74% yield as an analytically pure oil. The addition of bis(pentafluorophenyl)borane to 1 produces the fluorous boranes, 2a2b, as an analytically pure, isomeric mixture of anti-Markovnikov and Markovnikov hydroboration products in 38% isolated yield. Compounds 2a2b are soluble in both arene solvents and perfluoro(methylcyclohexane). Treatment of 2a2b with excess trimethylphosphine generates a mixture of products, including the Lewis adduct, 3, which can be isolated as an analytically pure oil in 15% yield. When exposed to either dimethylaminopyridine or piperidine at room temperature, the trimethylphosphine donor in 3 is cleanly displaced, based on in situ 31P NMR studies; under similar conditions, triethylamine does not react with 3. Addition of either dimethylaminopyridine or piperidine to 2a2b, followed by purification and subsequent treatment with an excess of either hydrogen chloride or p-toluenesulfonic acid, results in cleavage of the SiO linkages and the regeneration of 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-1-octanol.Key words: fluorous, borane, silane, Lewis acid.
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How this classification was reachedexpand
Full frame machine prediction
Teacher imitationNot calibrated prevalence, not ground truth. Human validation pending. The Gemma side is a direct model label for every work in the frame, read from the title-only record. The Codex side is a classifier learned from the 10,348 direct Codex labels and calibrated to design-weighted sample rates; fields without enough sample support carry no Codex call. Candidate is the union of the two sides; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels.
Distilled classifier scores by category (both heads)
| 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 | 0.001 |
| Open science | 0.000 | 0.001 |
| Research integrity | 0.001 | 0.001 |
| Insufficient payload (model declined to judge) | 0.004 | 0.002 |
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 source (direct Gemma or distilled Codex), 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".