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Record W1956496868 · doi:10.1002/047084289x.rn00375

2,2-Dimethyl-5-[3-(diphenylstannyl) propyl]-1,3-dioxolan-4-one

2004· reference-entry· en· W1956496868 on OpenAlex
Jian Wang, Derrick L. J. Clive

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

VenueEncyclopedia of Reagents for Organic Synthesis · 2004
Typereference-entry
Languageen
FieldChemistry
TopicOrganometallic Compounds Synthesis and Characterization
Canadian institutionsUniversity of Alberta
Fundersnot available
KeywordsChemistryReagentSodium borohydrideSolubilitySilica gelOrganic chemistryNuclear chemistryCatalysis

Abstract

fetched live from OpenAlex

[410098-22-5] C20H24O3Sn (MW 431.10) InChI = 1S/C8H13O3.2C6H5.Sn.H/c1-4-5-6-7(9)11-8(2,3)10-6;2*1-2-4-6-5-3-1;;/h6H,1,4-5H2,2-3H3;2*1-5H;; InChIKey = PUVIBBRSMWZAIC-UHFFFAOYSA-N (title reagent behaves similar to Bu3SnH and Ph3SnH in standard free radical reactions,1 but the tin-containing by-products can be removed easily from the desired reaction products by mild hydrolysis under basic or acidic conditions1) Physical Data: colorless oil. Solubility: soluble in common organic solvents; usually used in benzene or toluene. Preparative Methods: 2-hydroxy-4-pentenoic acid,2 prepared from glyoxylic acid hydrate, is ketalized using 2,2-dimethoxypropane and TsOH·pyridine; the ketal is hydrostannylated by heating with an excess of triphenyltin hydride, and treatment of the resulting stannane with 1 equiv of I2,3 followed by reduction with sodium borohydride, gives the title compound. Purification: rapid flash chromatography over silica gel, using 1:4 ethyl acetate–hexane, affords the stannane as a colorless oil.1 Handling, Storage, and Precautions: the compound can be stored1 for several months in a freezer (−10 °C) in a sealed flask flushed with nitrogen, without significant decomposition, and is easily repurified, if necessary, by flash chromatography. The toxicity of this compound has not been studied and, as a precaution, work with this compound should be done in a fume hood and skin contact should be avoided.

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)0.002
Version: codex-gemma-dda1882f352aValidation status: machine_predicted_unvalidated
Candidate categoriesMeta-epidemiology (narrow), Research integrity, Insufficient payload (model declined to judge)
Consensus categoriesnone
DomainCandidate signal: none · Consensus signal: none
Study designCandidate signal: Not applicable · Consensus signal: none
GenreCandidate signal: Other · Consensus signal: Other
Teacher disagreement score0.824
Threshold uncertainty score1.000

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0000.002
Meta-epidemiology (narrow)0.0010.001
Meta-epidemiology (broad)0.0020.001
Bibliometrics0.0000.001
Science and technology studies0.0000.000
Scholarly communication0.0000.000
Open science0.0010.000
Research integrity0.0010.001
Insufficient payload (model declined to judge)0.0330.000

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 head0.018
GPT teacher head0.233
Teacher spread0.215 · 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