Selective access to <i>p</i>-dialkyl-<i>carbo</i>-benzenes from a [6]pericyclynedione: the <i>n</i>-butyl nucleophile model for a metal switch study
Bibliographic record
Abstract
The synthesis, spectroscopic properties, comparative electrochemical behavior in CHCl3 vs CH2Cl2, and X-ray crystal structure of p-di-n-butyl-tetraphenyl-carbo-benzene are described. The selectivity of preparation of the ultimate [6]pericyclynediol precursor has been examined by comparing the reactivity of the [6]pericyclynedione substrate with four n-Bu-MXn nucleophiles involving more or less halogenated metal centers MXn (0 ≤ n ≤ 2): Li, MgBr, MgCl, CeCl2/LiCl. The cerium reagent is found to be the most efficient, giving approximately twice the yield given by Grignard reagents in the target diadduct (90% vs 51%–53%). The dibutyl-carbo-benzene product happens to be soluble in both CHCl3 and CH2Cl2: cyclic voltammograms of either solution exhibit almost identical peak potentials with reduced reversibility of the redox processes in CHCl3.
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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 | 0.000 |
| Open science | 0.000 | 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 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".