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Record W7106848981 · doi:10.1039/d5sc04462f

The versatile world of cumulene chemistry

2025· article· en· W7106848981 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.
fundA Canadian funder is recorded on the work.

Bibliographic record

VenueChemical Science · 2025
Typearticle
Languageen
FieldChemistry
TopicCyclization and Aryne Chemistry
Canadian institutionsUniversity of Alberta
FundersNatural Sciences and Engineering Research Council of CanadaNarodowa Agencja Wymiany AkademickiejNarodowe Centrum Nauki
KeywordsCumuleneRealmBridge (graph theory)Cognitive reframingOrganic synthesis

Abstract

fetched live from OpenAlex

]cumulenes, paying particular attention to the most accessible [3]cumulenes, alongside more limited but instructive examples of [4]- and [5]cumulenes, we demonstrate that these sp-hybridized frameworks offer exceptional synthetic versatility. Indeed, cumulenes can function effectively as nucleophiles, electrophiles, and dienophiles, enabling cyclooligomerization, cycloaddition, organometallic coupling, and other transformations. We describe how these reactions utilize the "naked" sp-hybridized carbon atoms of the cumulene and their substantial internal energy to access structurally diverse products that would otherwise be challenging or even impossible to obtain using more traditional routes. In doing so, we aim to showcase their potential in organic synthesis and highlight the opportunities they present for constructing novel molecular architectures. By reframing cumulenes as valuable synthetic building blocks, rather than mere curiosities, this review hopes to persuade chemists to incorporate these intriguing scaffolds more broadly into modern organic synthesis.

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 score0.407
Threshold uncertainty score0.913

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 studies0.0000.001
Scholarly communication0.0000.000
Open science0.0010.000
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 head0.005
GPT teacher head0.253
Teacher spread0.247 · 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