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- Title
Stereoselective Ring Opening of Electronically Excited Cyclohexa-2, 4-dienones: Cause and effect.
- Authors
Quinkert, Gerhard; Scherer, Stefan; Reichert, Dietmar; Nestler, Hans-Peter; Wennemers, Helma; Ebel, Andreas; Urbahns, Klaus; Wagner, Klaus; Michaelis, Klaus-Peter; Wiech, Gerhard; Prescher, Günter; Bronstert, Bernd; Freitag, Bernd-Jürgen; Wicke, Ilka; Lisch, Dietmar; Belik, Pavel; Crecelius, Thorsten; Hörstermann, Dirk; Zimmermann, Gottfried; Bats, Jan W.
- Abstract
The two conformers of a cyclohexa-2, 4-dienone with different substituents at C(6) on irradiation are believed to undergo ring opening stereospecifically affording a mixture of two configurationally isomeric diene-ketenes (and descendents thereof)- Exceptions are generally found for those dienones with one C and one O substituent or even with two C substituents, if one of them carries a polar group at a site able to interact through space with the ring CO group. In these cases, only one of the two anticipated diene-ketenes (and descendents thereof) is produced. A thorough investigation of the photochemistry of a series of structurally different cyclohexa-2, 4-dienones on analytical as well as on preparative scale extends our mechanistic knowledge of the various routes from diene-ketenes into a variety of compound classes. Novel compound classes accessible to diene-ketenes are seven-membered carbocycles (by intramolecular aldolization of the zwitterion of appropriately substituted, transiently formed diene-( N, O)-ketene acetals) and β-lactams (by Staudinger reaction).
- Publication
Helvetica Chimica Acta, 1997, Vol 80, Issue 6, p1683
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19970800602