Selective chemistry of tripentaerythritol Synthesis of acetals and their derivatives
Bibliographic record
Abstract
Tripentaerythritol was converted efficiently into 2′,2′′:6′,6′′:10′,10′′-tri-O-cyclohexylidene-2,2,6,6,10,10-hexakis(hydroxymethyl)-4,8-dioxa-1,11-undecandiol (4) by the toluenesulfonic acid catalysed reaction with cyclohexanone in a mixture of N,N-dimethylformamide and benzene. Reaction of tripentaerythritol with benzaldehyde under similar conditions gave an easily separated mixture of the four possible stereoisomers. Structures of these stereoisomers were assigned based on 1 H and 13 C NMR chemical shifts using trends previously observed for the dibenzylidene acetals of dipentaerythritol, whose structures had been established unambiguously by X-ray crystallography. It was found that reduction of the mixture of benzylidene acetals to 2,6,10-tris(benzyloxymethyl)-4,8-dioxa-1,11-undecanediol could be accomplished using triethylsilane with ethylaluminium dichloride as the Lewis acid after a number of commonly used conditions for this transformation failed.Key words: pentaerythritol, tripentaerythritol, dipentaerythritol, acetals, benzylidene acetals, reduction.
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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) | 0.000 | 0.000 |
| Meta-epidemiology (broad) | 0.001 | 0.000 |
| Bibliometrics | 0.000 | 0.000 |
| Science and technology studies | 0.000 | 0.001 |
| 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".