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Record W3157463505 · doi:10.1002/anie.202104595

A Divergent Strategy for Site‐Selective Radical Disulfuration of Carboxylic Acids with Trisulfide‐1,1‐Dioxides

2021· article· en· W3157463505 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

VenueAngewandte Chemie International Edition · 2021
Typearticle
Languageen
FieldChemistry
TopicSulfur-Based Synthesis Techniques
Canadian institutionsUniversity of Ottawa
Fundersnot available
KeywordsChemistryRadicalDecarboxylationHomolysisRadical substitutionAlkylSulfonylSubstitution reactionOrganic chemistryCombinatorial chemistryPhotochemistryCatalysis

Abstract

fetched live from OpenAlex

Abstract The direct conversion of carboxylic acids into disulfides is described. The approach employs oxidative photocatalysis for base‐promoted decarboxylation of the substrate, which yields an alkyl radical that reacts with a trisulfide dioxide through homolytic substitution. The trisulfide dioxides are easily prepared by a newly described approach. 1°, 2°, and 3° carboxylic acids with varied substitution are good substrates, including amino acids and substrates with highly activated C−H bonds. Trisulfide dioxides are also used to achieve the γ‐C(sp 3 )−H disulfuration of amides through a radical relay sequence. In both reactions, the sulfonyl radical that results from substitution propagates the reaction. Factors governing the selectivity of substitution at S2 versus S3 of the trisulfide dioxides have been explored.

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 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 score0.032
Threshold uncertainty score1.000

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)0.0010.000

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 head0.021
GPT teacher head0.274
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