ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Vinylogous β-Cleavage of Enones: UV.-irradiation of 4-(3′,7′,7′-trimethyl-2′-oxabicyclo[3.2.0]hept-3′-ene-1′-yl)but-3-ene-2-onOn 1π,π*-excitation (λ = 254 nm) in acetonitrile (E/Z)-2 is converted into the isomers 4-9 and undergoes fragmentation yielding 10; in methanol (E/Z)-2 gives 7-10 and is transformed into 11 by incorporation of the solvent.On 1π,π*-excitation (λ λ≥347 nm; benzene-d6) (E)-2 is isomerized into (Z)-2, which is converted into the isomers 3 and 4 by further irradiation.1π,π*-Excitation (λ = 254 nm; acetonitrile) of 4 gives 6 and (E)-9, whereas UV.-irradiation (λ = 254 nm; acetonitrile-d3) of 5 yields (E)-7 and 8.On 1π,π*-excitation (λ = 254 nm; acetonitrile) of (E/Z)-12 the compounds (E)-14 and (E)-15 are obtained.
Additional Material:
2 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19810640123