Direct Ketone Conversion to Cyclohexynes for Alkyne-Ene Reactions
Why this work is in the frame
A frame that forgets how it found something cannot be audited. These are the routes that admitted this work.
Bibliographic record
Abstract
Cyclohexynes are highly strained intermediates that are largely underexplored compared to benzynes as their aromatic counterparts. Previous strategies towards generating cyclohexynes include accessing precursors with specific functionality such as silyl vinyl triflates, vinyl halides, vinyl pseudohalides, diazirines, carbene precursors, or diacyl peroxides among others. Ultimately, the stepwise buildup of these starting materials and the transient nature of cyclohexynes has led to their synthetic utility being limited to specific classes of reactions including cycloadditions and nucleophilic trapping. To address these challenges, we envisioned accessing cyclohexynes directly from ketones, one of the most abundant and easy to install functional groups. In this work, we report forming cyclohexynes from ketones via a vinyl triflate intermediate formed in situ. These cyclohexynes then undergo a cyclohexyne-ene reaction, an unprecedented mode of reactivity for this strained intermediate. The work presented herein highlights an alternative strategy towards generating cyclohexynes and expands their synthetic utility.
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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) | 0.001 | 0.001 |
| Meta-epidemiology (broad) | 0.001 | 0.000 |
| Bibliometrics | 0.000 | 0.001 |
| Science and technology studies | 0.001 | 0.000 |
| Scholarly communication | 0.000 | 0.000 |
| Open science | 0.001 | 0.000 |
| Research integrity | 0.001 | 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 it