Evidence map›Paper›PMID 36937785›Full record

ArticleOrganometallics2023

Curious Case of Cobaltocenium Carbaldehyde.

Daniel Menia, Michael Pittracher, Holger Kopacka, Klaus Wurst, Florian R Neururer, Daniel Leitner, Stephan Hohloch, Maren Podewitz, Benno Bildstein

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In one paragraph

Article in Organometallics, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 3 papers.

0numbers the graph read from it
0cells of the map it votes in
3citing 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

3 citing papers in PubMed.

  1. Article
  2. Article
  3. Article
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

9 authors.

Daniel MeniaInstitut für Allgemeine, Anorganische und Theoretische Chemie, Universität Innsbruck, Innrain 80-82, 6020 Innsbruck, Austria.ORCID https://orcid.org/0000-0003-1134-5955
Michael PittracherInstitut für Allgemeine, Anorganische und Theoretische Chemie, Universität Innsbruck, Innrain 80-82, 6020 Innsbruck, Austria.
Holger KopackaInstitut für Allgemeine, Anorganische und Theoretische Chemie, Universität Innsbruck, Innrain 80-82, 6020 Innsbruck, Austria.
Klaus WurstInstitut für Allgemeine, Anorganische und Theoretische Chemie, Universität Innsbruck, Innrain 80-82, 6020 Innsbruck, Austria.
Florian R NeururerInstitut für Allgemeine, Anorganische und Theoretische Chemie, Universität Innsbruck, Innrain 80-82, 6020 Innsbruck, Austria.
Daniel LeitnerInstitut für Allgemeine, Anorganische und Theoretische Chemie, Universität Innsbruck, Innrain 80-82, 6020 Innsbruck, Austria.
Stephan HohlochInstitut für Allgemeine, Anorganische und Theoretische Chemie, Universität Innsbruck, Innrain 80-82, 6020 Innsbruck, Austria.ORCID https://orcid.org/0000-0002-5353-0801
Maren PodewitzInstitute of Materials Chemistry, TU Wien, Getreidemarkt 9, 1060 Vienna, Austria.ORCID https://orcid.org/0000-0001-7256-1219
Benno BildsteinInstitut für Allgemeine, Anorganische und Theoretische Chemie, Universität Innsbruck, Innrain 80-82, 6020 Innsbruck, Austria.ORCID https://orcid.org/0000-0003-1969-1334

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

Cobaltocenium carbaldehyde (formylcobaltocenium) hexafluoridophosphate, a long sought-after functionalized cobaltocenium salt, is accessible from cobaltocenium carboxylic acid by a three-step synthetic sequence involving (i) chlorination to the acid chloride, (ii) copper-borohydride reduction to the hydroxymethyl derivative, and (iii) Dess-Martin oxidation to the title compound. Due to the strongly electron-withdrawing cationic cobaltocenium moiety, no standard aldehyde reactivity is observed. Instead, nucleophilic addition followed by haloform-type cleavage prevails, thereby ruling out common useful aldehyde derivatization. One-electron reduction of cobaltocenium carbaldehyde hexafluoridophosphate affords the deep-blue, isolable cobaltocene carbaldehyde 19-valence-electron radical whose spin density is located fully at cobalt and not at the formyl carbon atom.

Identifiers

PMID36937785
PMCPMC10015550

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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.