76745-42-1Relevant academic research and scientific papers
The 193-nm Photochemistry of Some Fused-Ring Cyclobutenes: Absence of Orbital Symmetry Control
Dauben, William G.,Haubrich, Jeanne E.
, p. 600 - 606 (2007/10/02)
The photochemistry of cis-bicyclodec-9-ene (1), cis-bicyclodeca-2,9-diene (4), and trans-bicyclodeca-2,9-diene (8) has been examined at 193 nm in pentane solution.The photochemistry of 1 was complicated by the apparent formation of the thermally labile diene 15, which prevented direct determination of the primary photoproducts of 1.Dienes 4 and 8 were found to eliminate acetylene stereoselectively to give mainly the syn-elimination products 17 and 18, respectively.Ring opening of 4 and 8 gave, as primary products, trienes 5, 6, and 16, indicating that the stereospecificity suggested by the Woodward-Hoffmann rules of orbital symmetry was not followed.
