Synthesis and Structures of [2.<i>n</i>]Metacyclophan‐1‐enes and their Conversion to Highly Strained [2.<i>n</i>]Metacyclophane‐1‐ynes
Bibliographic record
Abstract
The syntheses of syn ‐[2. n ]metacyclophan‐1‐enes ( n = 5, 6, 8) in good yields using the McMurry cyclization of 1, n ‐bis(3‐formyl‐4‐methoxyphenyl)alkanes are reported. Conversion of syn ‐[2.6]‐ and [2.8]metacyclophan‐1‐enes to the corresponding highly strained syn ‐type [2.6]‐ and [2.8]metacyclophane‐1‐ynes was achieved by successive bromination and dehydrobromination reactions. An attempted trapping reaction of the putative corresponding [2.5]metacyclophane‐1‐yne by Diels–Alder reaction with 1,3‐diphenylisobenzofuran failed due to its smaller ring size and strained structure. X‐ray crystallographic analyses show that the triple bonds in syn ‐[2.6]‐ and [2.8]metacyclophane‐1‐ynes are distorted from linearity with bond angles of 156.7° and 161.4°, respectively. A DFT (Density Functional Theory) computational study was conducted to determine the stabilities of different conformations of the target compounds.
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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 | 0.000 |
| Scholarly communication | 0.000 | 0.000 |
| Open science | 0.001 | 0.000 |
| Research integrity | 0.000 | 0.000 |
| Insufficient payload (model declined to judge) | 0.001 | 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".