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- W1978376119 abstract "Die Hydrierwärme der olefinischen Doppelbindung in Bicyclo[2.1.0]pent-2-en (2) sowie im 5,5-Dimethylderivat 22 wird zu 42.5 bzw. 42.0 kcal mol−1 bestimmt. Durch Vergleich mit der Hydrierwärme der Doppelbindung von Bicyclo[2.2.0]hex-2-en (10) und Bicyclo[3.2.0]hept-6-en (9) ergibt sich für das Bicyclo[2.1.0]pent-2-en-System eine antiaromatische Destabilisierung von 10 kcal mol−1. Der antiaromatische Charakter von 2 zeigt sich auch in seiner hohen Reaktivität als Dienophil. 2 reagiert mit 1,3-Cyclopentadien (6) 4.5 × 104 mal schneller als Bicyclo[4.2.0]oct-7-en (8). Heats of Hydrogenation, II. Heats of Hydrogenation of Bicyclo[2.1.0]pent-2-ene, an Antiaromatic System The heat of hydrogenation of the olefinic double bond in bicyclo[2.1.0]pent-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 bicyclo[2.2.0]hex-2-ene (10) and bicyclo[3.2.0]-hept-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 bicyclo[4.2.0]oct-7-ene (8)." @default.
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- W1978376119 date "1980-05-01" @default.
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- W1978376119 title "Hydrierwärmen, II. Hydrierwärme des Bicyclo[2.1.0]pent‐2‐ens, ein antiaromatisches System" @default.
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- W1978376119 doi "https://doi.org/10.1002/cber.19801130517" @default.
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