Studies on Lewis‐Acid Induced Reactions of 8‐Methoxy[2.2]metacyclophanes: A New Synthetic Route to Alkylated Pyrenes
Bibliographic record
Abstract
Abstract Anti ‐8‐methoxy[2.2]metacyclophanes (MCPs) 5 a – b were obtained via pyrolysis of the corresponding syn ‐thiatetraoxide cyclophanes 4 a – b . Coupling reactions of 4‐ tert ‐butyl‐1‐methoxy‐2,6‐bis(mercaptomethyl)benzenes 1 a – b and 1,5‐bis(chloro‐methyl)‐2,4‐dimethylbenzene 2 under high dilution conditions afforded only the syn ‐conformers of 9‐methoxy‐2,11‐dithia[3.3]metacyclophanes 3 a – b , which with m ‐CPBA formed the corresponding syn ‐tetraoxides 4 a – b . Lewis acid (TICl 4 /AlCl 3 ‐MeNO 2 ) or iodine‐catalyzed reactions of 5 b under various conditions led to transannular cyclization to afford tetrahydropyrene 6 b and pyrene derivative 7 b and/or de‐ tert ‐butylated 6 a . Iodine‐catalyzed reaction of 5 a afforded tetrahydropyrene 6 a . These findings suggest the potential for a new route to alkylated pyrenes via strained and alkylated metacyclophanes. Density functional theory (DFT) studies were carried out to investigate the conformational characteristics of 3–5 .
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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 | 0.003 |
| 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 | 0.000 |
| Scholarly communication | 0.000 | 0.000 |
| Open science | 0.000 | 0.000 |
| Research integrity | 0.000 | 0.000 |
| Insufficient payload (model declined to judge) | 0.000 | 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".