Reactions of a Dilithiomethane with CO and N<sub>2</sub>O: An Avenue to an Anionic Ketene and a Hexafunctionalized Benzene
Bibliographic record
Abstract
Abstract Synthesis of value‐added products from simple C1 feedstocks is an attractive alternative avenue to traditional fossil fuels. Hexa‐substituted benzene derivatives are highly useful molecules but are often challenging to prepare. Herein, we report that the lithium complex [(Ph 2 P(S)) 2 CLi 2 (THF)] 2 1 reacts with CO lead to C−C bond formation and migration of a Ph 2 P( S )‐fragment affording 2 . Subsequent reaction with N 2 O results in oxidative cleavage of a P−C bond affording [Ph 2 P(S)OLi(THF) 2 ] 2 4 and the anionic ketene‐derivative Ph 2 P(S)CCOLi(THF) 2 5 . Heating 5 prompts cyclotrimerization giving the hexa‐substituted benzene derivative [Ph 2 P(S)CCOLi(THF) 2 ] 3 6 regioselectively. This transition metal‐free protocol to a hexa‐substituted benzene is viable on a gram scale and permits the incorporation of 13 C labels. The mechanisms of these reactions are detailed via extensive DFT computations.
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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 | 0.000 |
| 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 | 0.000 | 0.000 |
| Research integrity | 0.000 | 0.000 |
| 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".