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Chemiluminescence-promoted oxidation of alkyl enol ethers by NHPI under mild conditions and in the dark.

ABSTRACT: The hydroperoxidation of alkyl enol ethers using N-hydroxyphthalimide and molecular oxygen occurred in the absence of catalyst, initiator, or light. The reaction proceeds through a radical mechanism that is initiated by N-hydroxyphthalimide-promoted autoxidation of the enol ether substrate. The resulting dioxetane products decompose in a chemiluminescent reaction that allows for photochemical activation of N-hydroxyphthalimide in the absence of other light sources.

SUBMITTER: Anderson TE

PROVIDER: S-EPMC8117068 | biostudies-literature | 2021 Feb

REPOSITORIES: biostudies-literature

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Chemiluminescence-promoted oxidation of alkyl enol ethers by NHPI under mild conditions and in the dark.

Anderson T E TE Andia Alexander A AA Woerpel K A KA

Tetrahedron 20201224

The hydroperoxidation of alkyl enol ethers using N-hydroxyphthalimide and molecular oxygen occurred in the absence of catalyst, initiator, or light. The reaction proceeds through a radical mechanism that is initiated by N-hydroxyphthalimide-promoted autoxidation of the enol ether substrate. The resulting dioxetane products decompose in a chemiluminescent reaction that allows for photochemical activation of N-hydroxyphthalimide in the absence of other light sources. ...[more]

PMID: 33994596

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