Light as a traceless reagent in synthesis is currently being researched for developing more sustainable approaches in chemistry. Alkyl azides are an example of organic azides that can be used in visible-light driven reactions to make new C-N bonds forming heterocyclic compounds. However, the photoreactivity of alkyl azides needs to be further investigated to better understand their complex reaction mechanisms, that depend on factors such as the azide structure, irradiation wavelength, and whether the excitation takes place directly or indirectly through sensitizers. Specifically, 2,2-diazido-2,3-dihydroinden-1-one was investigated to determine its photoreactivity and to elucidate its reaction pathway. We used product studies, laser flash photolysis, ESR spectroscopy, cryogenic matrices, and density functional theory calculations to aid in proposing a reaction mechanism for the phototransformation of 2,2-diazido-2,3-dihydroinden-1-one. The proposed reaction mechanism will be presented in detail. Obtaining more knowledge on alkyl azides photoreactivity will contribute to the development of sustainable approaches in synthesis.

Photochemical and mechanistic investigation of 2,2-diazido-2,3-dihydroinden-1-one

ACS Spring 2022

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