Evidence map›Paper›PMID 36399366›Full record

ArticleAngewandte Chemie (International ed. in English)2023

Photochemical Decarbonylation of Oxetanone and Azetidinone: Spectroscopy, Computational Models, and Synthetic Applications.

Manvendra Singh, Pawan Dhote, Daniel R Johnson, Samuel Figueroa-Lazú, Christopher G Elles, Zarko Boskovic

Abstract read
In one paragraph

Article in Angewandte Chemie (International ed. in English), 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 1 paper.

0numbers the graph read from it
0cells of the map it votes in
1citing 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

1 citing paper in PubMed.

  1. Review
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.

Manvendra SinghDepartment of Medicinal Chemistry, University of Kansas, Lawrence, 66045, KS, USA.
Pawan DhoteDepartment of Medicinal Chemistry, University of Kansas, Lawrence, 66045, KS, USA.
Daniel R JohnsonDepartment of Chemistry, University of Kansas, Lawrence, 66045, KS, USA.
Samuel Figueroa-LazúIndependent researcher, Lawrence, 66044, KS, USA.
Christopher G EllesDepartment of Chemistry, University of Kansas, Lawrence, 66045, KS, USA.ORCID 0000-0002-1408-8360
Zarko BoskovicDepartment of Medicinal Chemistry, University of Kansas, Lawrence, 66045, KS, USA.ORCID 0000-0001-9376-527X

Funding

Synthetic Chemical Biology CoreP20GM113117 · NIGMS · UNIVERSITY OF KANSAS LAWRENCE · PI OROZCO, ROBIN C. · 2016 to 2025
$23.9M
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 RR019398NIGMS NIH HHS P20 GM113117
6 · The paper itself

Abstract

Photoexcitation of cyclic ketones leads to the expulsion of carbon monoxide and a mixture of products derived from diradical intermediates. Here we show that synthetic utility of this process is improved if strained heterocyclic ketones are used. Photochemistry of 3-oxetanone and N-Boc-3-azetidinone has not been previously described. Decarbonylation of these 4-membered rings proceeds through a step-wise Norrish type I cleavage of the C-C bond from the singlet excited state. Ylides derived from both compounds are high-energy species that are kinetically stable long enough to undergo [3+2] cycloaddition with a variety of alkenes and produce substituted tetrahydrofurans and pyrrolidines. The reaction has a sufficiently wide scope to produce scaffolds that were either previously inaccessible or difficult to synthesize, thereby providing experimental access to new chemical space.

Indexed as

AzetidinesKetonesComputer SimulationSpectrum Analysis2-azetidinoneAzetidinesKetonesComputational ModelsCycloadditionDecarbonylationKineticsPhotochemistry

Identifiers

PMID36399366
PMCPMC9839639

What OpenQuestion holds

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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.