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Record W2075154254 · doi:10.1021/om300410h

Diamido-Ether Actinide Complexes as Catalysts for the Intramolecular Hydroamination of Aminoalkenes

2012· article· en· W2075154254 on OpenAlex

Why this work is in the frame

A frame that forgets how it found something cannot be audited. These are the routes that admitted this work.

affAt least one author lists a Canadian institution in the pinned OpenAlex snapshot.

Bibliographic record

VenueOrganometallics · 2012
Typearticle
Languageen
FieldChemistry
TopicCatalytic Alkyne Reactions
Canadian institutionsUniversity of British ColumbiaSimon Fraser University
Fundersnot available
KeywordsHydroaminationChemistryIntramolecular forceMedicinal chemistryDiethyl etherEtherCatalysisAlkylationAlkylReactivity (psychology)ActinideHalideThoriumOrganic chemistryUraniumNuclear chemistry

Abstract

fetched live from OpenAlex

The synthesis and characterization of a series of new diamido-thorium(IV) and diamido-uranium(IV) halide and alkyl complexes supported by three different diamido-ether ligands are reported. Reaction of ThCl 4 ·2DME with [(RNSiMe 2 ) 2 O]Li 2 ([ R NON]Li 2 ) in DME when R = t Bu gives [ t Bu NON]ThCl 5 Li 3 ·DME ( 1 ), when R = i Pr 2 Ph in diethyl ether [ i Pr 2 Ph NON]ThCl 3 Li·DME ( 3 ) is prepared. Reaction of UCl 4 with [ i Pr 2 Ph NON]Li 2 in diethyl ether gives {[ i Pr 2 Ph NON]UCl 2 } 2 ( 4 ). Reaction of ThCl 4 ·2DME with Li 2 [( i Pr 2 PhNCH 2 CH 2 ) 2 O] ([ i Pr 2 Ph NCOCN]Li 2 ) in DME gives [ i Pr 2 Ph NCOCN]ThCl 2 ·DME ( 5 ). The addition of 2 equiv of LiCH 2 SiMe 3 to 1 and 5 resulted in salt- and base-free [ t Bu NON]Th(CH 2 SiMe 3 ) 2 ( 7 ) and [ i Pr 2 Ph NCOCN]Th(CH 2 SiMe 3 ) 2 ( 9 ), respectively. Complexes 1, 3, 4, 7, and 9, as well as previously reported {[ t Bu NON]UCl 2 } 2 ( 2 ), [ t Bu NON]U(CH 2 SiMe 3 ) 2 ( 6 ), and [ i Pr 2 Ph NCOCN]U(CH 2 SiMe 3 ) 2 ( 8 ) were examined as catalysts for the intramolecular hydroamination of a series of aminoalkenes. Complexes 6 – 9 were shown to facilitate the formation of 2-methyl-4,4-diphenylpyrrolidine from 2,2-diphenyl-1-amino-4-pentene at room temperature. For 9, this reaction occurs in less than 15 min, while for other dialkyls 6 – 8, the reaction takes less than 2 h. Dihalides 1 and 2 facilitated the same reaction at 60 °C in 4 h, while 3 and 4 showed no activity under the same conditions. Dialkyl complexes 7 – 9 were examined for further reactivity with different substrates. The uranium dialkyl 8 was more active than 7 and 9 for the cyclization of 2,2-diphenyl-1-amino-5-hexene and 2,2-diphenyl-1-amino-6-heptene, as well as more active in the cyclization of N -methyl-2,2-diphenyl-1-amino-4-pentene, a secondary amine. All three dialkyls became less active when the steric bulk of the gem -substituents was decreased from diphenyl to cyclopentyl; reactivity further decreased when the steric bulk of the substituents was decreased further to hydrogen.

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.

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 score0.055
Threshold uncertainty score0.537

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 studies0.0000.000
Scholarly communication0.0000.000
Open science0.0000.000
Research integrity0.0000.000
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 head0.019
GPT teacher head0.272
Teacher spread0.253 · 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