In Situ Generated 1‐Naphthylmethyl Radicals from Bis(1‐Naphthylmethyl)tin Dichlorides: Utilization for C−C, C−N, and C−O Bond‐Forming Reactions
Bibliographic record
Abstract
Abstract The in situ‐generated 1‐naphthylmethyl radicals from the thermolysis of bis(1‐naphthylmethyl)tin dichlorides combine with persistent organic radicals, 4‐hydroxy‐TEMPO or 4‐oxo‐TEMPO designs C−O bond forming products. Subsequently, the C−N bond occurs when the 1‐naphthylmethyl radicals unite with nitric oxide (NO) under a nitrogen atmosphere. In contrast, the oxidation instead of the addition reaction predominantly happens in the 1‐naphthylmethyl radicals when nitrogen dioxide contains a high oxidation state nitrogen center, i. e., N(IV) used. The by‐product, dodecanuclear organotin cages, with twelve peripheral naphthyl units, could be isolated from the 4‐hydroxy‐TEMPO reaction. Besides, the synthesis of unsymmetrical diarylmethanes RArCH 2 (R=1‐naphthyl, 2,4,6‐Me 3 C 6 H 2 , 3‐ and 4‐MeC 6 H 4 , phenyl, 4‐ClC 6 H 4 ; Ar=4‐MeOC 6 H 4 , 3,4‐, 2,4‐ and 2,5‐Me 2 C 6 H 3 ) in high yields and with good regioselectivity is reported. This new methodology involves the iodine‐mediated thermolysis of bis(arylmethyl)tin dichlorides (RCH 2 ) 2 SnCl 2 and an excess of an arene. This reaction involves homolytic cleavage of Sn−C bonds to give arylmethyl radicals that react with iodine in the presence of SnCl 2 to give the corresponding cations, which undergo electrophilic attack on the arene. Functionalised diarylmethanes have wide applications in pharmaceutical, agrochemical, and materials sciences. Alternative synthetic approaches to this class of organic compounds that avoid using a transition‐metal catalyst or a strong Lewis acid are desirable.
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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 | 0.002 |
| Meta-epidemiology (narrow) | 0.000 | 0.000 |
| Meta-epidemiology (broad) | 0.001 | 0.000 |
| Bibliometrics | 0.000 | 0.001 |
| Science and technology studies | 0.000 | 0.000 |
| Scholarly communication | 0.000 | 0.001 |
| Open science | 0.000 | 0.000 |
| Research integrity | 0.000 | 0.001 |
| Insufficient payload (model declined to judge) | 0.002 | 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".