Photochemistry of cyclopentadiene isolated in low-temperature argon matrices
The photochemistry of cyclopentadiene isolated in low-temperature argon matrices was studied by means of IR and UV/VIS spectroscopy. Bicyclo[2.1.0]pent-2-ene was formed by the irradiation of matrix-isolated cyclopentadiene using a super-high-pressure mercury lamp. When the matrix-isolated cyclopentadiene was irradiated with shorter wavelength using a low-pressure mercury lamp, further reactions of bicyclo[2.1.0]pent-2-ene were found to produce allylacetylene and vinylallene. While the photochemistry of cyclopentadiene to form bicyclo[2.1.0]pent-2-ene is known in a solution system, the production of allylacetylene and vinylallene in a matrix-isolated system has never been previously reported. The assignments of the species and the determination of the reaction mechanisms were performed using molecular orbital calculations.
Miyazaki, Jun,Yamada, Yasuhiro
p. 145 - 153
(2007/10/03)
Dewar Furan and Dewar Thiophene: Low-Temperature Matrix Photolysis of Furan and Thiophene
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Rendall, W. A.,Clement, A.,Torres, M.,Strausz, O. P.
p. 1691 - 1692
(2007/10/02)
Heats of Hydrogenation, II. Heats of Hydrogenation of Bicyclopent-2-ene, an Antiaromatic System
The heat of hydrogenation of the olefinic double bond in bicyclopent-2-ene (2) and in the 5,5-dimethyl derivative 22 has been determined (42.5 and 42.0 kcal mol-1).By comparison with the heat of hydrogenation of the double bond in bicyclohex-2-ene (10) and bicyclohept-6-ene (9) an antiaromatic destabilisation of 10 kcal mol-1 is demonstrated.The antiaromaticity of 2 is also manifested in its high dienophilic reactivity.The rate of the reaction of 2 with 1,3-cyclopentadiene (6) is enhanced by a factor of 4.5 * 104 compared to the analogous reaction of bicyclooct-7-ene (8).
Roth, Wolfgang R.,Klaerner, Frank-Gerrit,Lennartz, Hans-Werner
p. 1818 - 1829
(2007/10/02)
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