Intramolecular <i>ortho</i> Photocycloaddition of 4-Substituted 7-(4′-Alkenyloxy)-1-indanones and Ensuing Reaction Cascades
Bibliographic record
Abstract
High Resolution Image Download MS PowerPoint Slide 4-Substituted 7-(4′-alkenyloxy)-1-indanones were prepared from the respective substituted aryl propanoic acids and subjected to UV-A irradiation (λ = 350 or 366 nm). While the 4-chloro compound was directly converted at λ = 366 nm into a pentacyclic product (47% yield) by a three-photon cascade process, the oxygenated substrates reacted in trifluoroethanol at λ = 350 nm by a two-photon cascade, involving an ortho photocycloaddition, a thermal disrotatory ring opening, and a [4π] photocyclization (six examples, 67–82% yield). An ensuing photochemical di-π-methane rearrangement of the latter products was achieved by irradiation at λ = 350 nm in toluene (five examples, 36–70% yield). The diastereoselectivity of the reaction was probed employing a chiral 1-indanone with a stereogenic center at carbon atom C3. 1-Indanones with a 4-hexenyloxy side chain [( E )- or ( Z )-configured] at carbon atom C7 served to interrogate the stereospecifity of the reaction.
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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) | 0.000 | 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 | 0.001 |
| 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".