Novel Copolymers of Trisubstituted Ethylenes and Styrene. II. Halogen Ring‐Substituted Ethyl 2‐Cyano‐1‐oxo‐3‐phenyl‐2‐propenylcarbamates
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Bibliographic record
Abstract
Abstract Electrophilic trisubstituted ethylenes (TSE), halogen ring‐substituted ethyl 2‐cyano‐1‐oxo‐3‐phenyl‐2‐propenylcarbamates, RC6H4CH˭C(CN)CONHCO2C2H5 (where R is 3‐Br, 4‐Br, 3‐Cl, 4‐Cl, 2‐F, 3‐F, and 4‐F) were prepared and copolymerized with styrene (ST). The monomers were synthesized by the piperidine catalyzed Knoevenagel condensation of ring‐substituted benzaldehydes and N‐cyanoacetylurethane, and characterized by CHN analysis, IR, 1H, and 13C NMR. All the ethylenes were copolymerized with ST (M1) in solution with radical initiation (AIBN) at 70°C. The compositions of the copolymers were calculated from nitrogen analysis and the structures were analyzed by IR, 1H, and 13C NMR. The order of relative reactivity (1/r 1) for the monomers is 2‐F (3.81) > 3‐Cl (1.36) > 4‐Br (1.31) > 3‐Br (1.13) > 4‐F (0.90) > 3‐F (0.63) > 4‐Cl (0.37). Higher T g of the copolymers in comparison with that of polystyrene indicates decrease in chain mobility of the copolymer due to the high dipolar character of the TSE structural unit. Gravimetric analysis indicated that the copolymers decompose in the range 303–319°C. Keywords: Trisubstituted ethylenesRadical copolymerizationStyrene copolymersCarbamates Acknowledgments We are grateful to acknowledge that the project was partly supported by the Coatings Industry Education Fund (CIEF), Chicago Society of Coating Technology and Office of Sponsored Programs and Research of DePaul University.
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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 | 0.001 | 0.000 |
| Meta-epidemiology (narrow) | 0.000 | 0.000 |
| Meta-epidemiology (broad) | 0.000 | 0.000 |
| Bibliometrics | 0.000 | 0.001 |
| Science and technology studies | 0.000 | 0.001 |
| Scholarly communication | 0.000 | 0.001 |
| Open science | 0.001 | 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