Phospha-Mannich reactions of RPH<sub>2</sub>, R<sub>2</sub>PH, and R<sub>3</sub>P
Bibliographic record
Abstract
Phosphorus-based Mannich-type reactions (phospha-Mannich reactions) of primary or secondary phosphines with carbonyl compounds and amines (R2NH, RNH2, and NH3) provide a powerful synthetic tool in the worldwide search for future ligands. The variety of amines and phosphines available allows for designing and fine-tuning water-soluble, chiral, macrocyclic, pincer, tripodal, photoactive, and etc., phosphine ligands with P–C–N linkage(s) (P,N-acetals). Aminized supports and amine-terminated dendrimers can easily be phosphine-functionalized by phospha-Mannich reactions, and used in reusable heterogeneous catalysts. If CH2O is used as a C-component, its stable adducts with phosphines, that is, RP(CH2OH)2 and R2PCH2OH, are often used in syntheses of P,N-acetals as they are less toxic and non-pyrophoric analogs of the phosphines, whereas other carbonyl compounds are usually converted into imines or iminium salts. In phospha-Mannich reactions, tertiary phosphines form a P+–C–N linkage (P+,N-acetals) that can easily be broken by bases, realizing imine, or iminium cations, and are used as imine/iminium donors in organic syntheses.
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How this classification was reachedexpand
Full frame machine prediction
Teacher imitationNot calibrated prevalence, not ground truth. Human validation pending. The Gemma side is a direct model label for every work in the frame, read from the title-only record. The Codex side is a classifier learned from the 10,348 direct Codex labels and calibrated to design-weighted sample rates; fields without enough sample support carry no Codex call. Candidate is the union of the two sides; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels.
Distilled classifier scores by category (both heads)
| Category | Codex | Gemma |
|---|---|---|
| Metaresearch | 0.000 | 0.000 |
| Meta-epidemiology (narrow) | 0.001 | 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 | 0.001 |
| Open science | 0.000 | 0.000 |
| Research integrity | 0.000 | 0.001 |
| Insufficient payload (model declined to judge) | 0.004 | 0.001 |
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 source (direct Gemma or distilled Codex), 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".