On the Staudinger Reaction of SP(N<sub>3</sub>)<sub>3</sub> with PPh<sub>3</sub> and(Me<sub>3</sub>Si)<sub>2</sub>N–(Me<sub>3</sub>Si)N–PPh<sub>2</sub>
Bibliographic record
Abstract
Abstract The Staudinger reactions of SP(N 3 ) 3 ( 1 ) with 1, 2 and 3 equiv. of triphenylphosphane PPh 3 and (TMS) 2 N–(TMS)N–PPh 2 ( 2 ) have been investigated (TMS = Me 3 Si). Reaction with PPh 3 yields the single and double Staudinger products SP(N 3 ) 2 NPPh 3 ( 3 ) and SP(N 3 )(NPPh 3 ) 2 ( 4 ), but not the triple, while the reaction with 2 results only in the formation of the single Staudinger product SP(N 3 ) 2 NPPh 2 [N(TMS)N(TMS)] 2 ( 5 ). Compound 5 is air‐ and moisture‐sensitive but stable under argon over a long period in the solid state and in common organic solvents. Although there are covalently bound azide groups in 3 , 4 and 5 , these Staudinger products are neither shock‐ nor heat‐sensitive in contrast to 1 . Furthermore 3 , 4 and 5 are easily prepared in bulk (yield > 95 %), and unlimitedly stable when cooled and stored in the dark. Compound 5 is thermally stable up to over 150 °C while 3 and 4 are stable only up to 96 °C. However, when a solution of 5 is heated, a new surprising eight‐membered ring ( 6 ) is formed in an intermolecular TMS–N 3 elimination reaction. The structure and bonding is discussed on the basis of experimental X‐ray data and theoretical B3LYP calculations (thermodynamics, energy landscape and charge distribution). (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
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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 | 0.006 | 0.002 |
| Meta-epidemiology (narrow) | 0.005 | 0.005 |
| Meta-epidemiology (broad) | 0.006 | 0.003 |
| Bibliometrics | 0.001 | 0.004 |
| Science and technology studies | 0.002 | 0.002 |
| Scholarly communication | 0.002 | 0.002 |
| Open science | 0.005 | 0.002 |
| Research integrity | 0.002 | 0.007 |
| Insufficient payload (model declined to judge) | 0.001 | 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; both teacher heads agree on what is shown here.
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".