Stability, Reactivity, Solution, and Solid-State Structure of Halomethylzinc Alkoxides
Why this work is in the frame
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Bibliographic record
Abstract
In this paper, we report our findings regarding the development of a Lewis acid-catalyzed cyclopropanation of allylic alcohols with bis(iodomethyl)zinc. Iodomethylzinc alkoxides can be formed by treatment of an alcohol with bis(iodomethyl)zinc. These species are not prone to undergo cyclopropanation at low temperature but the addition of a Lewis acid in catalytic amounts induces the cyclopropanation reaction. Using this procedure, we demonstrated that the Lewis acid-catalyzed pathway significantly overwhelms the uncatalyzed one. This paper describes fundamental issues regarding the preparation and stability of halomethyl zinc alkoxides in solution as well as their aggregation state in solution and solid-state structures. Furthermore, the competition reaction between the inter- vs intramolecular cyclopropanation will be studied. Finally, we will discuss the possible activation pathways to explain the Lewis acid activation of halomethylzinc alkoxides. These findings provided new insights on the reactivity of ROZnCH(2)I and established the groundwork for the elaboration of an enantioselective version of the reaction.
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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 | 0.001 |
| Scholarly communication | 0.000 | 0.000 |
| Open science | 0.000 | 0.000 |
| Research integrity | 0.000 | 0.001 |
| Insufficient payload (model declined to judge) | 0.000 | 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