Tert-Butoxide-Mediated Protodeformylation of Tertiary Homobenzaldehydes
Year: 2021
Type: preprint
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.
Authors: Xiao Cai, Benjamin J. Stokes
Institution: University of California, Merced
Language: English
Topic: Chemical Reaction Mechanisms
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: green
OpenAlex ID: W3193643367