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.
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.
Source:
PAC, 2007, 79, 293
(Glossary of terms used in photochemistry, 3rd edition (IUPAC Recommendations 2006))
on page 305
InChI=1/C5H9N/c1-3-4-5-6-2/h3,5H,1,4H2,2H3/b6-5+
InChI=1/C5H9N/c1-6-4-5-2-3-5/h4-5H,2-3H2,1H3/b6-4+
InChI=1/C5H9N/c1-3-5-6-4-2/h3-4H,1,5H2,2H3/b6-4+
InChI=1/C5H9N/c1-2-6-5-3-4-5/h2,5H,3-4H2,1H3/b6-2+
InChI=1/C5H9N/c1-3-6-4-5(6)2/h3,5H,1,4H2,2H3
KLQZFXJMIBGQMI-AATRIKPKBB
CVNLVOYZUWDKNL-GQCTYLIABG
XXDBKYOGCNWTGK-GQCTYLIABO
LFFVJQCIBUZGEI-QHHAFSJGBP
FWOVFWAZHKSVHY-UHFFFAOYAK
Cite as:
IUPAC. Compendium of Chemical Terminology, 2nd ed. (the "Gold Book"). Compiled by
A. D. McNaught and A. Wilkinson. Blackwell Scientific Publications, Oxford (1997).
XML on-line corrected version: http://goldbook.iupac.org (2006-) created by M. Nic,
J. Jirat, B. Kosata; updates compiled by A. Jenkins. ISBN 0-9678550-9-8.
https://doi.org/10.1351/goldbook.
