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di-π-methane rearrangement

Photochemical reaction of a molecular entity comprising two π-systems, separated by a saturated carbon atom (a 1,4-diene or an allyl-substituted aromatic analogue), to form an ene- (or aryl-) substituted cyclopropane.
Note:
The rearrangement formally amounts to a 1,2 shift of one ene group (in the diene) or the aryl group (in the allyl-aromatic analogue) and 'bond formation' between the lateral carbons of the non-migrating moiety.
D01745
Source:
PAC, 2007, 79, 293 (Glossary of terms used in photochemistry, 3rd edition (IUPAC Recommendations 2006)) on page 325
InChI=1/C5H8/c1-3-5-4-2/h3-4H,1-2,5H2
InChI=1/C5H8/c1-2-5-3-4-5/h2,5H,1,3-4H2
QYZLKGVUSQXAMU-UHFFFAOYAD
YIWFBNMYFYINAD-UHFFFAOYAL
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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. doi:10.1351/goldbook.
Last update: 2014-02-24; version: 2.3.3.
DOI of this term: doi:10.1351/goldbook.D01745.
Original PDF version: http://www.iupac.org/goldbook/D01745.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 The PDF version is out of date and is provided for reference purposes only.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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