The First Lateral Functionalization of Calix[4]arenes by a Homologous Anionic Ortho-Fries Rearrangement
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Bibliographic record
Abstract
Treatment of calix[4]arene bis- O -carbamates 4a, b − 6a, b with LDA in THF results in the regio- and stereoselective introduction of both axial and equatorial carboxamide groups at the methylene bridges via a homologous anionic ortho-Fries rearrangement to give 7 − 16 . The stereochemical outcome of the rearrangement is dependent on the reaction conditions and the conformation of the starting material. Stereochemical and structural proof has been secured by the X-ray crystal structure of calix[4]arene 10 having only one equatorial carboxamide moiety. The use of this novel class of methylene bridge-functionalized calix[4]arenes is illustrated by the formation of bis-γ-lactone 19, while the enhanced acidity of the remaining hydroxyl groups, owing to the presence of axial carboxamide groups at the methine bridges, followed from the easy propylation of bisrearranged calix[4]arene 7 .
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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 | 0.000 |
| 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 | 0.001 | 0.000 |
| Research integrity | 0.000 | 0.000 |
| Insufficient payload (model declined to judge) | 0.011 | 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