Phospha-Mannich reactions of PH <sub>3</sub> and its analogs
Why this work is in the frame
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Bibliographic record
Abstract
The easiest route to form compounds with P–Csp3–N linkage(s) is phosphorus-based Mannich-type reactions (phospha-Mannich reactions) between phosphines (R3P, R2PH, RPH2, PH3), carbonyl compounds (mainly CH2O) and amines (R2NH, RNH2, NH3). Because of toxicity and inflammability, applications of PH3 and its liquid analog (Me3Si)3P in such reactions are rare. Stable, less toxic, and non-pyrophoric adducts of PH3 with CH2O, i.e., tris(hydroxymethyl)phosphine (HOCH2)3P and tetrakis(hydroxymethyl)phosphonium (HOCH2)4P+ salts, are often used as both P- and C-sources in phospha-Mannich reactions, providing many acyclic and cyclic P,N-ligands, among which 1,3,5-triaza-7-phosphaadamantane (PTA) is most known. Phospha-Mannich reactions of (HOCH2)4P+ salts with urea form condensation products that are used to impart fire retardance to cotton materials, the most important and oldest area of application of the salts. The use of (HOCH2)3P and (HOCH2)4P+ salts as cross-linking agents in protein-based hydrogel manufacturing, enzyme immobilization on NH2-containing supports, and leather tanning, is also based on phospha-Mannich reactions and ability to form P–CH2–N linkages with amino acids residues. Mechanistic aspects of phospha-Mannich reactions are discussed.
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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) | 0.001 | 0.000 |
| Bibliometrics | 0.000 | 0.000 |
| Science and technology studies | 0.001 | 0.000 |
| Scholarly communication | 0.000 | 0.000 |
| Open science | 0.000 | 0.000 |
| Research integrity | 0.000 | 0.001 |
| Insufficient payload (model declined to judge) | 0.001 | 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