Bibliographic record
Abstract
[38227-87-1] C9H18LiN (MW 147.22) (strong, highly hindered, nonnucleophilic base (pKa = 37.3)1 capable of selective deprotonation of aromatics, heteroaromatics, and aliphatic CH acidic sites in the presence of a variety of functional groups; also compatible with several electrophiles for in situ quenching of kinetically derived lithiated species2-5) Alternate Names: LiTMP; LTMP. Physical Data: exists in THF solution as a dimer–monomer equilibrium mixture; additives such as HMPA increase monomer concentration.6, 7 X-ray structure determination shows that LiTMP crystallizes as a tetramer from hexane/pentane mixtures.8 Solubility: sol most organic solvents including THF, Et2O, hexane. Preparative Method: prepared in Et2O or THF solutions immediately before use by treatment of commercially available dry 2,2,6,6‐Tetramethylpiperidine with n‐Butyllithium (1∶1). Tetramethylpiperidine is dried by heating a mixture of the base with CaH2 at reflux for 4 h in a preflamed flask, followed by distillation at atmospheric pressure (bp 152 °C). It should be stored in a septum sealed bottle. Handling, Storage, and Precautions: LiTMP solutions are pyrophoric, can cause severe burns, and should always be handled and transferred under an inert atmosphere. Solutions of LiTMP show a loss of activity (50% in THF; 60% in Et2O) after 12 h at 24 °C.9 Use in a fume hood.
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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 | 0.004 |
| Meta-epidemiology (narrow) | 0.001 | 0.001 |
| Meta-epidemiology (broad) | 0.001 | 0.001 |
| Bibliometrics | 0.000 | 0.000 |
| Science and technology studies | 0.000 | 0.000 |
| Scholarly communication | 0.000 | 0.000 |
| Open science | 0.001 | 0.000 |
| Research integrity | 0.001 | 0.001 |
| Insufficient payload (model declined to judge) | 0.054 | 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".