Reaction of tris(hydroxymethyl)phosphine and cinnamaldehyde in methanol
Bibliographic record
Abstract
Abstract Reaction of tris(hydroxymethyl)phosphine with excess cinnamaldehyde in CH3OH or CD3OD, followed using NMR, proceeds via several phosphorus‐containing intermediates, multiple transformations of organic parts, and with the solvent H/D isotope effect on products. In both solvents, one CH2OH group of tris(hydroxymethyl)phosphine is readily replaced by the cinnamaldehyde moiety to give the primary product, a 1,3‐oxaphosphorinane derivative. Slower replacement of the second CH2OH group leads to a mixture of aliphatic and heterocyclic phosphine intermediates in a ratio of ~4:1 in CH3OH and ~1:1 in CD3OD; both intermediates contain alcohol and aldehyde groups and convert rapidly into intra‐ and intermolecular hemiacetals. The hemiacetals of the aliphatic phosphine rearrange further into an unsymmetrical trialkylphosphine oxide, whereas the hemiacetals of the heterocyclic phosphine react with the third mole of cinnamaldehyde to replace the third CH2OH group of tris(hydroxymethyl)phosphine. All intermediates and products are formed as mixtures of stereoisomers.
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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) | 0.000 | 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) | 0.002 | 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".