A Case of Competitive Aromatization vs. Sigmatropic [1,5]-Hydrogen Atom Migration in a 1,2,4-Cyclohexatriene Intermediate Derived from a Bis-Enyne Cyclization.

Abstract read

In one paragraph

Article in Molecules (Basel, Switzerland), 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

0numbers the graph read from it

0cells of the map it votes in

0citing papers in PubMed

–field-weighted citation impact

1 · What the graph read from it

What it found

Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.

The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.

2 · The registry

The trial behind it

Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.

Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.

3 · Its place in the literature

Who cites it

0 citing papers in PubMed.

No citing paper in PubMed yet.

4 · The record

Corrections and comments

PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.

5 · Who and what money

Authors and funding

3 authors.

Rong TangDepartment of Chemistry, University of Minnesota, Minneapolis, MN 55455, USA.ORCID 0009-0000-7982-3568

Qian XuDepartment of Chemistry, University of Minnesota, Minneapolis, MN 55455, USA.

Thomas R HoyeDepartment of Chemistry, University of Minnesota, Minneapolis, MN 55455, USA.ORCID 0000-0001-9318-1477

Funding

Women's CancerP30CA077598 · NCI · UNIVERSITY OF MINNESOTA TWIN CITIES · PI Douglas Yee · 1998 to 2026

$100.4M

Synthesis, Structure, and Mechanism of Biorelevant Molecules and ReactionsR35GM127097 · NIGMS · UNIVERSITY OF MINNESOTA · PI THOMAS R. HOYE · 2018 to 2026

$3.5M

Upgrade of a 500 MHz NMR Spectrometer for Applications in Biomedical ResearchS10OD011952 · OD · UNIVERSITY OF MINNESOTA · PI HOYE, THOMAS R. · 2012 to 2012

$378k

NCI NIH HHS P30 CA077598NIGMS NIH HHS R35 GM127097NIH Cancer Center Support Grant P30 CA77598NIH HHS 1R35GM127097-24NIH HHS S10 OD011952

6 · The paper itself

Abstract

1,2,4-Cyclohexatrienes are strained, reactive intermediates often formed by the tetradehydro-Diels-Alder (TDDA) reaction of a conjugated enyne bearing a tethered alkyne as the enynophile. The ene component is commonly the π-bond of an aromatic group. In this focused study, we investigated the reactivity of a symmetrical substrate in which the pair of terminal ene moieties were simple 2-propenyl groups. The intermediate 1,2,4-cyclohexatriene, now bearing a 5-isopropenyl group, underwent competitive aromatization (the most usual outcome of the strain-relieving event of the cyclohexatriene), along with an intramolecular [1,5]-hydrogen atom migration, ultimately producing a non-benzenoid, pyrrole derivative. This represents a previously unknown process for a 1,2,4-cyclohexatriene derivative. Mechanistic aspects of the competitive processes were revealed by experiments performed in the presence of various protic additives (MeOD and BHT).

Indexed as

strain-promoted reactionstetradehydro-Diels–Alder (TDDA)thermal rearrangements

Identifiers

PMID40572572

DOI10.3390/molecules30122610

PMCPMC12195621

What OpenQuestion holds

Textmetadata

LicenceCC BY

Read underepoch 390

Registered trials

None linked

Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.