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Record W1986672150 · doi:10.1021/ja1064153

Reactions of Boron Amidinates with CO<sub>2</sub> and CO and Other Small Molecules

2010· article· en· W1986672150 on OpenAlexaff
M.A. Dureen, Douglas W. Stephan

Bibliographic record

VenueJournal of the American Chemical Society · 2010
Typearticle
Languageen
FieldChemistry
TopicOrganoboron and organosilicon chemistry
Canadian institutionsUniversity of Toronto
Fundersnot available
KeywordsChemistryCarbodiimideBoraneHeterolysisMedicinal chemistryBoronIsopropylThermal decompositionYield (engineering)MoleculeStereochemistryOrganic chemistryCatalysis

Abstract

fetched live from OpenAlex

Reaction of Piers' borane, HB(C(6)F(5))(2), with either tert-butyl or isopropyl carbodiimide cleanly affords the boron amidinates HC(RN)(2)B(C(6)F(5))(2) [R = iPr (1), tBu (2)]. These species undergo a variety of insertion reactions. For example, treatment of 1 with CO(2) or excess carbodiimide gives HC(iPrN)(2)(CO(2))B(C(6)F(5))(2) (3) or HC(iPrN)(2)C(iPrN)(2)B(C(6)F(5))(2) (4), respectively. Similarly, exposure of 1 or 2 to 1 atm CO gives HC(RN)(2)(CO)B(C(6)F(5))(2) [R = iPr (5), tBu (6)], while reaction of 1 with CNtBu gives HC(RN)(2)(CNtBu)B(C(6)F(5))(2) [R = iPr (7), tBu (8)]. Compounds 1 and 2 also react with benzaldehyde, resulting in the formation of HC(RN)(2)(PhHCO)B(C(6)F(5))(2) [R = iPr (9), tBu (10)]. Compound 1 also reacts with MeCN to give HC(iPrN)(2)(MeCN)B(C(6)F(5))(2) (11) and effects heterolytic C-H cleavage to afford HC(iPrN)(iPrNH)(PhCC)B(C(6)F(5))(2) (12). In contrast, the species PhC(iPrN)(2)B(C(6)F(5))(2) (14) derived from PhC(iPrN)(2)BCl(2) (13) failed to react with any of the above substrates. These data, in addition to the isolation of HC(iPrN)(2)(C(6)F(4))BF(C(6)F(5)) (15), the product of thermolysis of 1, provide further support for the notion that the transient "open-chain" form of these amidinates is present in solution.

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 imitation

Not 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.

metaresearch head score (Codex)0.000
metaresearch head score (Gemma)0.000
Version: codex-gemma-dda1882f352aValidation status: machine_predicted_unvalidated
Candidate categoriesnone
Consensus categoriesnone
DomainCandidate signal: none · Consensus signal: none
Study designCandidate signal: Bench or experimental · Consensus signal: Bench or experimental
GenreCandidate signal: Empirical · Consensus signal: Empirical
Teacher disagreement score0.018
Threshold uncertainty score0.408

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0000.000
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0000.000
Bibliometrics0.0000.000
Science and technology studies0.0000.001
Scholarly communication0.0000.000
Open science0.0000.000
Research integrity0.0000.001
Insufficient payload (model declined to judge)0.0000.000

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.

Opus teacher head0.006
GPT teacher head0.224
Teacher spread0.218 · how far apart the two teachers sit on this one work
Validation statusscore_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from it

Classification

machine, unvalidated

Machine predicted; a candidate call from one teacher head, not a consensus.

The models applied no category: nothing in the taxonomy fit this work.
Study designBench or experimental
Domainnot available
GenreEmpirical

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".

Quick stats

Citations216
Published2010
Admission routes1
Has abstractyes

Explore more

Same venueJournal of the American Chemical SocietySame topicOrganoboron and organosilicon chemistryFrench-language works237,207