M. Tada, T. Kokubo, Tadashi Sato*
Jul 1, 1970
Citations
0
Influential Citations
10
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
Methyl acetoacetate was irradiated in the presence of cyclohexene to afford methyl 3-cyclohexyl-3-hydroxybutyrate (VIII), methyl 3-cyclohexenyl-3-hydroxybutyrate (IX), two oxetanes (Xa and Xb), and cyclohexene dimers. In contrast to acetylacetone, acetoacetate behaves as a saturated ketone rather than as an α,β-unsaturated ester on photoreaction. We concluded that the n-π* excitation of the enol-form of β-dicarbonyl compound is responsible for photo-cycloaddition, and no effective n–π* excitation is accesisble on irradiaron of the enol-form of acetoacetate, since the enol form of acetoacetate has its n–π* and π-π* absorptions in the same region.