134834-47-2Relevant academic research and scientific papers
Photochemistry of Cyclic Enones. Part 8. 5-(But-3-enyl)-3-phenylcyclopent-2-enone and 5-(Pent-4-enyl)-3-phenylcyclopent-2-enone
McMurry, T. Brian H.,Work, Annemarie,McKenna, Brian
, p. 811 - 816 (2007/10/02)
Photolysis of 5-(but-3-enyl)-3-phenylcyclopent-2-enone in benzene solution using Pyrex filter affords two products in the ratio 2:1.These are 1-phenyltricyclo3,8>nonan-7-one and 8-phenyltricyclo3,8>nonan-9-one.They are inseparable by column chromatogryphy, but their structure follows from examination of the four separable lactones derived from the mixture by Baeyer-Villiger oxidation.Photolysis of 5-(pent-4-enyl)-3-phenylcyclopent-2-enone under the same conditions affords only one product, 9-phenyltricyclo3.9>decan-10-one, whose structure follows from examination of the two lactones derived by similar oxidation.These results demonstrate that in these compounds the regioselectivity of ring depends on the length of the 5-side-chain.
