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Photooxidation of 2-(tert-Butyl)-3-Methyl-2,3,5,6,7,8-Hexahydroquinazolin-4(1H)-one, an Example of Singlet Oxygen ene Reaction.

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.

SUBMITTER: Mendez A 

PROVIDER: S-EPMC7662339 | biostudies-literature | 2020 Oct

REPOSITORIES: biostudies-literature

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Photooxidation of 2-(<i>tert</i>-Butyl)-3-Methyl-2,3,5,6,7,8-Hexahydroquinazolin-4(<i>1H</i>)-one, an Example of Singlet Oxygen <i>ene</i> Reaction.

Méndez Adrian A   Valdez-Camacho Jonathan Román JR   Escalante Jaime J  

Molecules (Basel, Switzerland) 20201029 21

Singlet oxygen <i>ene</i> reactions produce 2-(<i>tert</i>-butyl)-4a-hydroperoxy-3-methyl-2,4a, 5,6,7,8-hexahydroquinazolin-4(3<i>H</i>)-one quantitatively during diffusion crystallization of 2-(<i>tert</i>-butyl)-3-methyl-2,3,5,6,7,8-hexahydroquinazolin-4(1<i>H</i>)-one in <i>n</i>-hexane/CH<sub>2</sub>Cl<sub>2</sub> solvent mixture. To confirm this photo-oxidation, a <sup>1</sup>H-NMR study in CDCl<sub>3</sub> was performed with exposure to ambient conditions (light and oxygen), with neither a  ...[more]

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