" /> aza-di-π-methane rearrangement - CISMeF





Preferred Label : aza-di-π-methane rearrangement;

IUPAC definition : i Photochemical reaction /i of a 1-aza-1,4-diene or a 2-aza-1,4-diene in the triplet excited state to form the corresponding cyclopropylimine.;

Scope note : the rearrangement formally amounts to a 1,2-shift of the imino group and bond formation between the c(3) and c(5) carbon atoms of the azadiene skeleton. 1-aza-1,4-dienes also undergo the rearrangement to cyclopropylimines using electron-acceptor and electron-donor sensitizers via radical-cation and radical-anion intermediates, respectively. 2-aza-1,4-dienes rearrange to n-vinylaziridines on irradiation using electron-acceptor sensitizers. in this instance the reaction amounts to a 1,2-shift of the alkene unit and “bond formation? between the c(1) and c(3) carbon atoms of the azadiene skeleton.;

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i Photochemical reaction /i of a 1-aza-1,4-diene or a 2-aza-1,4-diene in the triplet excited state to form the corresponding cyclopropylimine.

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27/07/2025


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