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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.
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.
AT07329
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+
KLQZFXJMIBGQMI-AATRIKPKBB
InChI=1/C5H9N/c1-6-4-5-2-3-5/h4-5H,2-3H2,1H3/b6-4+
CVNLVOYZUWDKNL-GQCTYLIABG
InChI=1/C5H9N/c1-3-5-6-4-2/h3-4H,1,5H2,2H3/b6-4+
XXDBKYOGCNWTGK-GQCTYLIABO
InChI=1/C5H9N/c1-2-6-5-3-4-5/h2,5H,3-4H2,1H3/b6-2+
LFFVJQCIBUZGEI-QHHAFSJGBP
InChI=1/C5H9N/c1-3-6-4-5(6)2/h3,5H,1,4H2,2H3
FWOVFWAZHKSVHY-UHFFFAOYAK
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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. doi:10.1351/goldbook.
Last update: 2014-02-24; version: 2.3.3.
DOI of this term: doi:10.1351/goldbook.AT07329.
Original PDF version: http://www.iupac.org/goldbook/AT07329.pdf. The PDF version is out of date and is provided for reference purposes only. For some entries, the PDF version may be unavailable.
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