74295-57-1Relevant articles and documents
Photochemical reactions of 1-acetyl-3-methylbicyclobutane
Cerfontain, Hans,Geenevasen, Jan A. J.
, p. 386 - 394 (2007/10/02)
The photochemistry of 1-acetyl-3-methylbicyclobutane in various solvents using λ 254 and 300 nm radiation has been studied.In inert solvents, photoisomerization occurs with formation of 3 and 4 with subsequent photoconversion of 3 into 5.The (3 + 5)/4 ratios are significantly greater for λ 254 than for λ 300 nm radiation, illustrating direct reaction from the ??* excited state(s).Additional photoreduction to 6 was observed for λ 300 nm in hydrogen-donating solvents, especially in diisopropyl ether and toluene.In carbon tetrachloride, at λ 300 nm, mainly the HCl addition compound 10 is formed via ketone-photosensitized decomposition of CCl4.Similarly, with methanol, 2-propanol and water as solvent or addendum, the 1,3-addition products 7-9 are obtained.Under all of these conditions, no photoproducts containing the intact bicyclobutyl group were found, illustrating the high chemical reactivity of this severely strained group.Mechanisms for the formation of the photoisomerization, photoreduction and 1,3-dipolar addition products are proposed.
