Aryl(trimethylsilyl)selenides as Reagents for the Synthesis of Mono- and Diselenoesters
Bibliographic record
Abstract
Silylated organoselenium reagents react under mild conditions with acid chlorides to provide a high yield route to aromatic selenoesters. The synthesis, structures, and spectroscopic properties of the selenoesters C 6 H 5 SeC(O)R (R = CH 2 CH 3, 1; p -CH 3 C 6 H 4, 2; p -C 6 Me 4 Br, 3; p -C 6 Me 4 C(O)SeC 6 H 5, 4 ) and RC(O)SeFcSeC(O)R (Fc = Fe(C 5 H 4 ) 2; R = CH 2 CH 3, 5; p -CH 3 C 6 H 4, 6; p -BrC 6 Me 4, 7 ) and RC(O)Se(C 6 H 4 ) n SeC(O)R ( n = 1, R = CH 2 CH 3, 8a; n = 2, R = CH 2 CH 3, 8b; n = 1, R = p -CH 3 C 6 H 4, 9a; n = 2, R = p -CH 3 C 6 H 4, 9b; n = 1, R = p -C 6 Me 4 Br, 10a; n = 2, R = p -C 6 Me 4 Br, 10b ) and C 6 H 5 SeC(O)CH 2 CH 2 C(O)SeC 6 H 5 11 are discussed. Although 11 can be prepared in high yield from the reaction of C 6 H 5 SeSiMe 3 and ClC(O)CH 2 CH 2 C(O)Cl in tetrahydrofuran solvent, similar reactions in the absence of solvent led to the competitive formation of both 11 and (C 6 H 5 Se) 3 CCH 2 CH 2 C(O)OSiMe 3 12 . The new selenoesters have been characterized by multinuclear NMR ( 1 H, 13 C, 77 Se), IR, and UV–vis spectroscopies, electrospray mass spectrometry, and, for complexes 2, 4, 7, 10b, and 12, single-crystal X-ray diffraction.
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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 | 0.001 |
| Insufficient payload (model declined to judge) | 0.003 | 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".