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Record W1980428800 · doi:10.1021/om990650f

Probing the Effect of Organic and Organometallic Functionalization on [1,5]-Silicon Shifts in Indenylsilanes

2000· article· en· W1980428800 on OpenAlexaff
Mark Stradiotto, Paul Hazendonk, Alex D. Bain, Michael A. Brook, Michael J. McGlinchey

Bibliographic record

VenueOrganometallics · 2000
Typearticle
Languageen
FieldChemistry
TopicCatalytic Alkyne Reactions
Canadian institutionsMcMaster University
Fundersnot available
KeywordsChemistryTrimethylsilylIndeneSiliconMedicinal chemistryYield (engineering)Nuclear magnetic resonance spectroscopyChromiumChemical shiftStereochemistryOrganic chemistryPhysical chemistry

Abstract

fetched live from OpenAlex

Indenylsilanes bearing organic and organometallic substituents have been prepared in order to probe the effect of substitution on the rate of [1,5]-silicon shifts in this class of compounds. In an attempt to prepare 1,1,3-tris(trimethylsilyl)indene ( 7 ), the hitherto unknown silicon-functionalized bis(trimethylsilyl)dibenzo[ a, d ]fulvalene ( 9 ) was unexpectedly generated; this species was characterized by use of both NMR spectroscopy and X-ray crystallography and was rationally prepared in 68% yield from 3,3‘-bis(1-(trimethylsilyl))indene ( 16 ). The molecular dynamics of 1,3-dimethyl-1-(trimethylsilyl)indene ( 18 ) and the crystallographically characterized chromium complex (η 6 -1,3-dimethyl-1- exo -(trimethylsilyl)indene)tricarbonylchromium ( 22 ) were examined by use of 1D-selective inversion and 2D-EXSY NMR techniques; surprisingly, the presence of chromium and methyl substituents has a negligible effect on the rate of [1,5]-silicon shifts ( Δ G ⧧ = 23−24 kcal mol - 1 ) versus the parent compound 1-(trimethylsilyl)indene ( 3 ) ( Δ G ⧧ ≈ 24 kcal mol - 1 ). In the case of 18, the intermediate isoindene 18- iso was intercepted with tetracyanoethylene as the crystallographically characterized [4 + 2] cycloadduct 5,6-benzo-2,2,3,3-tetracyano-1,4-dimethyl-7-(trimethylsilyl)bicyclo(2.2.1)hept-5-ene ( 19 ).

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 categoriesInsufficient payload (model declined to judge)
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 score0.061
Threshold uncertainty score0.993

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0000.000
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0000.000
Bibliometrics0.0000.001
Science and technology studies0.0000.000
Scholarly communication0.0000.000
Open science0.0000.000
Research integrity0.0000.000
Insufficient payload (model declined to judge)0.0080.000

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 head0.007
GPT teacher head0.212
Teacher spread0.205 · 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.

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

Citations22
Published2000
Admission routes1
Has abstractyes

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