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- Title
Photochemische Reaktionen. 105. Mitteilung [1]. Zur Photochemie optisch aktiver λ, δ-Epoxy-enone: Racemisierung und Cyclisierung von (−)-4-Methyliden-5,6-epoxy-5,6-dihydro-β-jonon und (−)-4-Oxo-5,6-epoxy-5,6-dihydro-β-jonon
- Authors
Frei, Bruno; Wolf, Hans Richard; Jeger, Oskar
- Abstract
The photochemistry of optical active λ, δ-epoxy-enones. Racemization and cyclization of (−)-4-methylidene-5,6-epoxy-5,6-dihydro-β-ionone and of (−)-4-oxo-5,6-epoxy-5,6-dihydro-β-ionone UV.-irradiation (λ ≥ 347 nm as well as λ = 254 nm) converts the conjugated λ, δ-epoxy-enones (−)- 2 and (−)- 4 by cleavage of the C,C-oxirane bond to an intermediate ketonium ylide f which cyclizes giving the racemic starting materials. The degree of racemization depends on the length of the irradiation time. The formation of the optical active products (−)- 3 and (+)- 5 in these irradiations gives evidence, that the photocyclization of (−)- 2 und (−)- 4, respectively, is a one step reaction of a state g.
- Publication
Helvetica Chimica Acta, 1979, Vol 62, Issue 5, p1668
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19790620533