Temperature‐Assisted Generation of Arylmethyl Radicals from Bis(arylmethyl)tin Dichlorides: Efficient Reagents for − Bond‐Forming Reactions
Bibliographic record
Abstract
Abstract The oxidative‐addition reaction between an arylmethyl chloride (RCH2Cl; R=1‐C10H7, 2,4,6‐Me3C6H2, 4‐MeC6H4, 3‐MeC6H4, C6H5, 4‐ClC6H4) and tin powder in boiling toluene produces bis(arylmethyl)tin dichlorides, [(RCH2)2SnCl2] in good yields. At 160 °C in mesitylene bis(1‐naphthylmethyl)tin dichloride undergoes Sn−C homolytic cleavage to generate two 1‐naphthylmethyl radicals (1‐C10H7CH2⋅) which were trapped by TEMPO (C9H8NO⋅). Subsequently, the radicals (RCH2⋅) produced in this manner were utilized for efficient substitution reactions with electron‐rich arenes (R′H; R′=2,4,6‐Me3C6H2, 1,2,4,5‐Me4C6H, 1,2,3,4,5‐Me5C6) to obtain a variety of unsymmetrical diarylmethanes (RR′CH2). The addition of one equivalent of iodine (I2) to the reaction mixture resulted in a significant increase in the yields of coupled products.
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How this classification was reachedexpand
Full frame machine prediction
Teacher imitationNot calibrated prevalence, not ground truth. Human validation pending. The Gemma side is a direct model label for every work in the frame, read from the title-only record. The Codex side is a classifier learned from the 10,348 direct Codex labels and calibrated to design-weighted sample rates; fields without enough sample support carry no Codex call. Candidate is the union of the two sides; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels.
Distilled classifier scores by category (both heads)
| 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) | 0.002 | 0.001 |
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 source (direct Gemma or distilled Codex), 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".