Evidence map›Paper›PMID 38354334›Full record

ArticleThe Journal of organic chemistry2024

Twisted Intramolecular Charge-Transfer State Addition to Electron-Poor Olefins.

Mauricio Bahena Garcia, Manvendra Singh, Elizabeth Miller, Sarah Neuenswander, Justin Douglas, Zarko Boskovic

Abstract read
In one paragraph

Article in The Journal of organic chemistry, 2024. 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

6 authors.

Mauricio Bahena GarciaDepartment of Medicinal Chemistry, University of Kansas, Lawrence, Kansas 66045, United States.
Manvendra SinghDepartment of Medicinal Chemistry, University of Kansas, Lawrence, Kansas 66045, United States.
Elizabeth MillerDepartment of Medicinal Chemistry, University of Kansas, Lawrence, Kansas 66045, United States.
Sarah NeuenswanderNuclear Magnetic Resonance Laboratory, University of Kansas, Lawrence, Kansas 66045, United States.
Justin DouglasNuclear Magnetic Resonance Laboratory, University of Kansas, Lawrence, Kansas 66045, United States.
Zarko BoskovicDepartment of Medicinal Chemistry, University of Kansas, Lawrence, Kansas 66045, United States.ORCID 0000-0001-9376-527X

Funding

Synthetic Chemical Biology CoreP20GM113117 · NIGMS · UNIVERSITY OF KANSAS LAWRENCE · PI OROZCO, ROBIN C. · 2016 to 2025
$23.9M
Avance II 500 High Performance Digital NMR Spectrometer SystemS10RR024664 · NCRR · UNIVERSITY OF KANSAS LAWRENCE · PI VANDERVELDE, DAVID G · 2007 to 2007
$468k
Open access ESI-TOF/MS and GC/MS for organic chemistsS10RR019398 · NCRR · UNIVERSITY OF KANSAS LAWRENCE · PI WILLIAMS, TODD D · 2004 to 2004
$333k
NCRR NIH HHS S10 RR019398NCRR NIH HHS S10 RR024664NIGMS NIH HHS P20 GM113117
6 · The paper itself

Abstract

When electron-rich arylpyrrolinium salts are irradiated with ultraviolet light in the presence of Michael acceptors, the pyrrolinyl and aryl fragments add to the activated and polarized double bond in a regioselective manner, forming two C-C bonds and fragmenting the substrate. In this paper, we present a model for this intriguing reaction, supported by spectroscopy and computational analyses, and provide evidence for rectifying previously misassigned structures. We postulate that the photochemical reaction is inefficient because the reaction between the twisted intramolecular charge-transfer state and the olefin competes with fluorescence from this state upon photon absorption. We also discuss the practical advantages of performing this photochemical reaction in a continuous flow setup. Additionally, we explore several subsequent reactions that allow us to further modify the products of the photochemical step, ultimately leading to the creation of new chemical structures.

Identifiers

PMID38354334
PMCPMC11006016

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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.