The Thioether–Methyleneborane (PhSCH<sub>2</sub>B(C<sub>6</sub>F<sub>5</sub>)<sub>2</sub>)<sub>2</sub>: Synthesis and Reactivity with Donors and Alkynes
Bibliographic record
Abstract
2-Bromothioanisole, or thioanisole, was lithiated and subsequently reacted with ClB(C 6 F 5 ) 2 to yield a new compound with the empirical formulation PhSCH 2 B(C 6 F 5 ) 2, 1 . NMR data at low temperature as well as X-ray crystallographic data confirmed this species to be the dimer (PhSCH 2 B(C 6 F 5 ) 2 ) 2, although an equilibrium governs the interconversion of monomer to dimer at room temperature. Compound 1 reacts with P t Bu 3 or OPEt 3 to form adducts PhSCH 2 B(C 6 F 5 ) 2 (L) (L = P t Bu 3 2, OPEt 3 3 ) in 85% and 87% yield, respectively. Compound 1 also reacts with alkynes, namely, PhCCH, C 4 H 9 CCH, PhCCC 4 H 9, C 2 H 5 CCC 2 H 5, and PhCCPh, to give the species (PhSCH 2 B(C 6 F 5 ) 2 )(R′C═CR) (R = H, R′ = Ph 4, C 4 H 9 5, R = Ph, R′ = C 4 H 9 6, R = R′ = C 2 H 5 7, Ph 8 ) in yields in the range 70–92%. X-ray crystallographic analysis of 8 confirmed the five-membered zwitterionic heterocyclic formulation.
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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 | 0.002 | 0.002 |
| Meta-epidemiology (narrow) | 0.004 | 0.004 |
| Meta-epidemiology (broad) | 0.004 | 0.001 |
| Bibliometrics | 0.001 | 0.003 |
| Science and technology studies | 0.002 | 0.003 |
| Scholarly communication | 0.001 | 0.002 |
| Open science | 0.003 | 0.002 |
| Research integrity | 0.003 | 0.004 |
| Insufficient payload (model declined to judge) | 0.000 | 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".