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Record W2015653116 · doi:10.1021/om990845n

Reactions of the Binuclear Complexes [MIr(CO)<sub>3</sub>(Ph<sub>2</sub>PCH<sub>2</sub>PPh<sub>2</sub>)<sub>2</sub>] (M = Rh, Ir) with Alkyl Halides:  Dramatic Reactivity Differences as a Function of Metal Combination and Alkyl Halide

2000· article· en· W2015653116 on OpenAlexaff
Jeffrey R. Torkelson, Okemona Oke, John Waititu. Muritu, Robert McDonald, Martín Cowie

Bibliographic record

VenueOrganometallics · 2000
Typearticle
Languageen
FieldChemistry
TopicOrganometallic Complex Synthesis and Catalysis
Canadian institutionsUniversity of Alberta
FundersCentre National de la Recherche Scientifique
KeywordsChemistryTrifluoromethanesulfonateIodideIridiumAlkylMedicinal chemistryMethyleneMethyl iodideYield (engineering)Oxidative additionHalideLigand (biochemistry)MetalRhodiumStereochemistryOrganometallic chemistryCatalysisInorganic chemistryOrganic chemistry

Abstract

fetched live from OpenAlex

Reactions of [Ir 2 (CO) 3 (dppm) 2 ] ( 1; dppm = Ph 2 PCH 2 PPh 2 ) with CH 3 I and CH 3 OCH 2 I give the oxidative-addition products [Ir 2 (R)(I)(CO)(μ-CO)(dppm) 2 ] (R = CH 3 ( 3 ), CH 2 OCH 3 ( 4 )). The X-ray structure determination of 4 ·CH 2 Cl 2 shows that the alkyl group is the sole terminal ligand on one metal while the iodo and a carbonyl are terminally bound to the adjacent metal. The mixed-metal analogue [RhIr(CO) 3 (dppm) 2 ] ( 2 ) does not react with CH 3 I but reacts with CH 3 OCH 2 I to give [RhIr(CH 2 OCH 3 )(I)(CO)(μ-CO)(dppm) 2 ] ( 5 ). Reaction of 3 or 5 with methyl triflate results in iodide abstraction to yield the known compound [Ir 2 (CH 3 )(CO)(μ-CO)(dppm) 2 ][CF 3 SO 3 ] and [RhIr(CH 2 OCH 3 )(CO)(μ-CO)(dppm) 2 ][CF 3 SO 3 ] ( 8 ), respectively. In the mixed-metal compound iodide removal results in migration of the methoxymethyl group from Rh to Ir. Iodide abstraction from 4 results in a double C−H bond activation to yield the methoxycarbyne-bridged [Ir 2 (H) 2 (CO) 2 (μ-COCH 3 )(dppm) 2 ][CF 3 SO 3 ] ( 6 ). In the reactions of 4 and 5 with methyl triflate some methoxide abstraction also occurs, yielding the methylene-bridged products [MIr(CO) 2 (μ-CH 2 )(μ-I)(dppm) 2 ][CF 3 SO 3 ] (M = Ir ( 7 ), Rh ( 9 )) as minor products in between 15 and 30% yield. The reactions of [MIr(CO) 3 (dppm) 2 ] (M = Ir ( 1 ), Rh ( 2 )) with CH 2 I 2 and ICH 2 CN yield [MIr(CO) 2 (μ-I)(μ-CO)(Ph 2 PCHPPh 2 )(dppm)] (M = Ir ( 10 ), Rh ( 11 )) together with CH 3 I and CH 3 CN, respectively, by hydrogen abstraction from one of the dppm ligands and iodine atom coordination at the metals. Reactions of 1 with allyl bromide and benzyl bromide yield the bromo analogue [Ir 2 (CO) 2 (μ-Br)(μ-CO)(Ph 2 PCHPPh 2 )(dppm) 2 ] ( 12 ). The X-ray structure of 10 ·THF has been determined and shows a planar Ir−P−C(H)−P−Ir moiety, short P−C bonds (1.72(2) Å), and a 122(1)° angle at carbon of the Ph 2 PC(H)PPh 2 ligand, as expected for sp 2 hybridization and partial multiple-bond character in the P−C bonds.

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)0.002
metaresearch head score (Gemma)0.001
Version: codex-gemma-dda1882f352aValidation status: machine_predicted_unvalidated
Candidate categoriesMeta-epidemiology (narrow), Science and technology studies, Insufficient payload (model declined to judge)
Consensus categoriesMeta-epidemiology (narrow)
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 score0.058
Threshold uncertainty score1.000

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0020.001
Meta-epidemiology (narrow)0.0020.002
Meta-epidemiology (broad)0.0040.002
Bibliometrics0.0010.004
Science and technology studies0.0020.002
Scholarly communication0.0010.002
Open science0.0020.001
Research integrity0.0010.002
Insufficient payload (model declined to judge)0.0010.000

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 head0.012
GPT teacher head0.204
Teacher spread0.192 · 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; both teacher heads agree on what is shown here.

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

Citations26
Published2000
Admission routes1
Has abstractyes

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