Bis(ether) derivatives of tetrakis(2-hydroxyphenyl)ethene — Direct synthesis of (<i>E</i>)- and (<i>Z</i>)-bis(2-hydroxyphenyl)-bis(2-methoxyphenyl)ethene via the McMurry olefination reaction
Bibliographic record
Abstract
The direct synthesis of sterically hindered, partially etherified derivatives of tetrakis(2-hydroxyphenyl)ethene is reported by using the McMurry reductive olefination reaction on a range of differentially substituted 2,2′-dialkoxy benzophenone substrates. Three orthogonal protection strategies are demonstrated, incorporating β-silylethyl, 3-butenyl, and tert-butyl protecting groups, respectively, into the starting benzophenones. The latter proved most efficient, with both the McMurry coupling and deprotection steps occurring concomitantly under the McMurry conditions to directly yield the desired bis(2-hydroxyphenyl)-bis(2-methoxyphenyl)ethene as a 1:1 mixture of E- and Z-diastereoisomers.Key words: preorganized polyaryloxide ligands, McMurry olefination, titanium trichloride, supramolecular chemistry, tetrakis(2-hydroxyphenyl)ethene, 2,2′-disubstituted benzophenone.
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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 | 0.001 | 0.001 |
| Meta-epidemiology (narrow) | 0.001 | 0.000 |
| Meta-epidemiology (broad) | 0.001 | 0.001 |
| Bibliometrics | 0.000 | 0.001 |
| Science and technology studies | 0.000 | 0.001 |
| Scholarly communication | 0.000 | 0.000 |
| Open science | 0.001 | 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".