Journal of Organic Chemistry p. 4287 - 4289 (1983)
Update date:2022-08-17
Topics:
Washburn, William N.
The pKa's per hydrogen of bicyclo<3.2.1>octadiene (1), bicyclo<3.2.1>octene (2), bicyclo<3.2.2>nonadiene (5), and bicyclo<3.2.2>nonatriene (6), as measured in cyclohexylamine, were 31.4, >40.5, 34.0, and 32.0, respectively.The enhanced acidity of diene 1 corresponds to a stabilization of at least 12.2 kcal relative to the anion of 2, thus emphasizing the importance of homoaromaticity for suitable allylic anions.
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