aza-di-π-methane rearrangement
Photochemical reaction of a 1-aza-1,4-diene or a 2-aza-1,4-diene in the triplet excited state to form the corresponding cyclopropylimine.
The @R05194@ 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-@D01699@ also undergo the @R05194@ to cyclopropylimines using electron-acceptor and electron-donor @S05610@ via radical-@C00907@ and radical-@A00358@ intermediates, respectively. 2-Aza-1,4-@D01699@ rearrange to N-vinylaziridines on @I03255@ 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.
See also: di-π-methane rearrangement, di-π-silane rearrangement, oxa-di-π-methane rearrangement
PAC, 2007, 79, 293. 'Glossary of terms used in photochemistry, 3rd edition (IUPAC Recommendations 2006)' on page 305 (