Bulky derivatives of boranes, boronic acids and boronate estersvia reaction with diazomethanes
Bibliographic record
Abstract
Reactions of the perfluoroarylboranes RB(C(6)F(5))(2) (R = C(6)F(5), Ph, Cl, OC(6)F(5)) with Me(3)SiCH(N(2)), (C(6)F(5))CH(N(2)) or Ph(2)C(N(2)) yield (C(6)F(5))(2)B(Me(3)SiCH(C(6)F(5))) 1, (C(6)F(5))B(Me(3)SiCH(C(6)F(5)))(2) 2, (C(6)F(5))B(Me(3)SiCH(C(6)F(5)))(Me(3)SiCH(C(6)H(5))) 3, (C(6)F(5))(2)B(CH(C(6)F(5))(2)) 4, ClB(C(6)F(5))(Ph(2)C(C(6)F(5))) 5 and (C(6)F(5)O)B(C(6)F(5))(Me(3)SiCH(C(6)F(5))) 6 as a result of single or double insertion of a Me(3)SiCH, C(6)F(5)CH or Ph(2)C fragment into a B-C bond of the respective borane. Reactions of one or two equivalents of ethyl α-diazomethylacetate with B(C(6)F(5))(3) yielded (Me)(C(6)F(5))(C=C)(OC(2)H(5))(OB(C(6)F(5))(2)) 8 and [(Me)(C(6)F(5))(C=C)(OC(2)H(5))](2)(O(2)B(C(6)F(5))) 9, in addition to the corresponding pyridine adducts (Me)(C(6)F(5))(C=C)(OC(2)H(5))(OB(C(6)F(5))(2))(py) 10 and [(Me)(C(6)F(5))(C=C)(OC(2)H(5))](2)(O(2)B(C(6)F(5)))(py) 11. Similarly, reaction of α-diazomethylacetate with BPh(3) yielded analogous products of borane reorganization, (Me)(C(6)H(5))(C=C)(OC(2)H(5))(OBPh(2)) 12 and was isolated as a mixture of E and Z-isomers whereas BPh(3) reacts with Me(3)SiCH(N(2)) and pyridine yielding (py)B(Ph(2)(Me(3)SiCH(Ph)) 7. Reactions of Ph(2)C(N(2)) with RB(OH)(2) (R = C(6)F(5), p-F-C(6)H(4), C(6)H(5)) yielded cyclic boroxines of the form [Ph(2)C(R)BO](3) (R = C(6)F(5) 13, p-FC(6)H(4) 14, C(6)H(5) 15) while reactions of the boronate esters (C(6)H(4)O(2))BR (R = C(6)F(5), p-F-C(6)H(4)) with three or five equivalents of Me(3)SiCH(N(2)) yielded (C(6)H(4)O(2))B(Me(3)SiCH(Ar)) (Ar = C(6)F(5) 16, p-F-C(6)H(4) 17) and [(Py)B(C(6)H(4)O(2))(Me(3)SiCH(Ar))] (Ar = C(6)F(5) 18, p-F-C(6)H(4), 19) upon complexation with pyridine. Reaction of HBCat and ClBCat with Ph(2)C(N(2)) yielded the products of B-H and B-Cl bond derivatization (C(6)H(4)O(2))B(Ph(2)CR) (R = H 20, Cl 21), while the triethylphosphine oxide adduct (Et(3)PO)B(C(6)H(4)O(2))(CPh(2)Cl) 22, is readily isolable.
Fetched live from OpenAlex and de-inverted. Abstracts are not stored in this database: the inverted indexes are 8.6 GB of the frame’s 9.3 GB of text, and the host has 13 GB free.
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 | 0.000 | 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) | 0.001 | 0.000 |
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 teacher head, 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".