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.;
Origin ID : AT07329;
See also
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.
