A relationship between the catalytic carbonylation of (<i>N</i>-arenesulfonyl)imides and iodonium ylides
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Bibliographic record
Abstract
Reactivities of various sulfonamide derivatives of general formula ArSO 2 N=XPh n (X = I; n = 1; X = S, Se, n = 2; X = P, As, n = 3) in catalytic carbonylations have been explained by structural properties of the substrates. Based on crystallographic data reported in the literature, it has been concluded that the two-step catalytic oxidative carbonylation of sulfonylimides proceeds only when the N=X double bond is strongly polarized. The structural requirement observed within the sulfonamide derivatives has been found to be applicable for iodonium ylides. Catalytic carbonylation of the phenyliodonium methylide (3a) prepared from dimedone (5,5-dimethyl-1,3-cyclohexanedione) and (diacetoxyiodo)benzene, resulted in a new spirobenzofuranone derivative (5a) which was characterized by X-ray single crystal diffraction, 1 J C,C coupling constants, 13 C-T 1 relaxation times, as well as by IR and Raman spectroscopic methods. Crystals of 5a are monoclinic, space group P2 1 /c, a = 7.187(1), b = 21.129(1), and c = 10.636(1) Å, beta = 92.81(1)°, V = 1613.2(3) Å 3 , and Z = 4. A ketene intermediate has been postulated in the catalytic carbonylation of the iodonium ylide. A survey of databases has revealed that the triacyl dihydrofuranone moiety in 5a constitutes a new structural unit.Key words: oxidative carbonylation, palladium catalyst, iodonium ylides, spirobenzofuranone.
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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 | 0.001 |
| 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) | 0.000 | 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