Anton V. Chernykh, D. Radchenko, A. V. Chernykh
Sep 1, 2015
Citations
0
Influential Citations
12
Citations
Journal
European Journal of Organic Chemistry
Abstract
Hitherto unknown cis- and trans-3-alkyl- and 3-aryl-3-fluorocycobutylamines have been synthesised selectively from 3-oxocyclobutane carboxylic acid in six or seven steps. Comparison of their pKa and log D values with those of the fluorine-free parent compounds showed acidification by about 0.8 units, irrespective of the stereochemistry. This indicates that there are no through-space interactions between fluorine and the amino function – a conclusion that was supported by the results of X-ray analysis. Fluorinated trans-compounds were found to be more lipophilic (Δ log P ≈ 1) compared with the non-fluorinated analogues, whereas the difference was marginal for cis isomers.