Novel bis(isobenzofuran)s and their utility in the synthesis of cyclophanes
Bibliographic record
Abstract
The synthesis of l,2-bis(5-isobenzofuranyl)ethene by two routes is described.The first route involved generation of l,2-bis(5-isobenzofuranyl)ethene from a bis(acetal) precursor under basic conditions.However, the synthesis was lengthy with low-yielding steps, which led to it being abandoned.The second route involved generation of 1,2bis(5-isobenzofuranyl)ethene from a bis(oxabicyclic) precursor with 3,6-di(2'-pyridyl)-5'tetrazine.Naphtho[l,2-c:5,6-c]difuran and l,2-bis(5-isobenzofuranyl)ethene were used to construct novel cyclophanes by double Diels-Alder reactions with bis(maleimide)s.NMR, AMI modeling, and X-ray studies of the cyclophanes are discussed.Attempts to prepare phenanthro[2,3-c:6,7-c]difuran and its cyclophanes are discussed.None was successful, and investigations were hampered by the inability to obtain sufficient quantities of starting materials.Finally, several suggestions are given for improving the syntheses of l,2-bis(5isobenzofuranyl)ethene, phenanthro[2,3-c:6,7-c]difuran, and their cyclophanes.Future directions, such as the functionalization of the double bond of l,2-bis(5isobenzofuranyl)ethene, aromatization of the oxabicyclic rings of the cyclophanes, and further X-ray studies are discussed.crystallographic analysis, respectively.
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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 | 0.002 | 0.000 |
| 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 | 0.001 |
| Open science | 0.003 | 0.000 |
| Research integrity | 0.001 | 0.001 |
| 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".