74503-30-3Relevant academic research and scientific papers
Heats of Hydrogenation, II. Heats of Hydrogenation of Bicyclopent-2-ene, an Antiaromatic System
Roth, Wolfgang R.,Klaerner, Frank-Gerrit,Lennartz, Hans-Werner
, p. 1818 - 1829 (2007/10/02)
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).
