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Tert-Butoxide-Mediated Protodeformylation of Tertiary Homobenzaldehydes

26 August 2021, Version 1
Working Paper
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Tert-butoxide mediates the protodeformylation of tertiary homobenzaldehydes and related compounds at ambient temperature. Both geminal dialkyl and geminal diaryl substituents are tolerated. Monocyclic aromatic homobenzaldehydes require cyclic gem-dialkyls or gem-diaryls for efficient protodeformylation, whereas gem-dimethyls are sufficient for protodeformylation of polycyclic arenyl substrates. Our data suggest a stabilized radical is generated upon attack of the aldehyde by tert-butoxide.

Keywords

decarbonylation
tert-butoxide

Supplementary materials

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Stokes_2021_Protodeformylation_Supporting Information
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Supporting Information for 'Tert-Butoxide-Mediated Protodeformylation of Tertiary Homobenzaldehydes'
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Now Published

tert-Butoxide-Mediated Protodeformylative Decarbonylation of α-Quaternary Homobenzaldehydes [opens in a new tab]
Benjamin Stokes, Xiao Cai, Ritter V. Amsbaugh, Lauren J. Drake, Ravi M. A. Kotamraju, Nicholas Javier C. Licauco journal article
SynOpen

Version History

Aug 26, 2021 Version 1

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The content is available under CC BY NC ND 4.0 [opens in a new tab]

DOI

10.26434/chemrxiv-2021-q22x8
D O I: 10.26434/chemrxiv-2021-q22x8 [opens in a new tab]

Author’s competing interest statement

The author(s) have declared they have no conflict of interest with regard to this content

Ethics

The author(s) have declared ethics committee/IRB approval is not relevant to this content

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