Bergman Cyclization of Fluorinated Benzo‐Fused Enediynes to Naphthalene Derivatives: Syntheses and Structures
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Bibliographic record
Abstract
Abstract Fluorinated naphthalene derivatives were prepared by Bergman cyclization of fluorinated benzo‐fused enediynes. This route provides access to the aromatic target compounds in a two‐step procedure from commercially available precursors, via a Sonogashira cross‐coupling and a subsequent, thermally initiated Bergman cyclization. Crystal structures of six fluorinated benzo‐enediynes and three fluorinated naphthalene derivatives display significant diversity in their molecular structures and in the crystal packing arrangements. The rather subtle structural change from di‐ to tetrafluorobenzo‐enediynes, as well as the variation in the terminal acetylene subunit led to different non‐covalent interactions in the solid state that ultimately govern their crystal structures.
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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) | 0.000 | 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) | 0.006 | 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 it