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- Title
Photooxidation of 2-(tert -Butyl)-3-Methyl-2,3,5,6,7,8-Hexahydroquinazolin-4(1H)-one, an Example of Singlet Oxygen ene Reaction †.
- Authors
Méndez, Adrian; Valdez-Camacho, Jonathan Román; Escalante, Jaime; Neves, M. Graça P. M. S.; Favi, Gianfranco
- Abstract
Singlet oxygen ene reactions produce 2-(tert-butyl)-4a-hydroperoxy-3-methyl-2,4a, 5,6,7,8-hexahydroquinazolin-4(3H)-one quantitatively during diffusion crystallization of 2-(tert-butyl)-3-methyl-2,3,5,6,7,8-hexahydroquinazolin-4(1H)-one in n-hexane/CH2Cl2 solvent mixture. To confirm this photo-oxidation, a 1H-NMR study in CDCl3 was performed with exposure to ambient conditions (light and oxygen), with neither additional reactants nor catalysts. A theoretical study at the B3LyP/6311++G** level using the QST2 method of locating transition states suggests a two-step mechanism where the intermediate, which unexpectedly did not come from the peroxide intermediate, has a low activation energy.
- Subjects
REACTIVE oxygen species; ENE reactions; ACTIVATION energy; CRYSTALLIZATION; MIXTURES
- Publication
Molecules, 2020, Vol 25, Issue 21, p5008
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules25215008