Studies on the rearrangement of <i>ortho</i>-nitrobenzylidenemalonates and their Analogues to 2-aminobenzoate derivatives
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Bibliographic record
Abstract
Reaction of the diethyl 2-nitro-4-(trifluoromethyl)benzylidenemalonate with diethylamine in alcohols resulted in the reduction of the nitro group and the oxidation of the vinylic carbon attached to the phenyl ring. Simultaneous migration of the malonic fragment gave the appropriate 2-amino-4-(trifluoromethyl)benzoate esters. The presence of at least two nitro groups, or one nitro group and trifluoromethyl group on the phenyl ring, attached to the α-carbon and strongly electron withdrawing substituents at the β-carbon (CO 2 Et, CN) in ortho-nitrobenzylidene systems is necessary for this reductiveoxidative rearrangement to proceed. Reaction of nitrocinnamates with thiols in the presence of triethylamine in tetrahydrofuran gave Michael addition products with different regioselectivity of addition. Ethyl 2-nitrocinnamate undergoes standard β-addition of thiols to a carboncarbon double bond. However, 2,4-dinitro- and 2,4,6-trinitrocinnamates undergo α-addition of thiols, indicating that the presence of two nitro groups on the phenyl ring can reverse polarity of the carboncarbon double bond in cinnamate acceptors.Key words: abnormal Michael reactions, aromatic nitro compounds, benzylidene compounds, rearrangements.
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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) | 0.001 | 0.000 |
Machine scores (provisional)
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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