Extremely facile ring inversion and rearrangement in fluorobicyclo [2.1. 0] pentanes

Y Wei, Y Liu, T Wong, DM Lemal

Index: Wei, Yanjun; Liu, Yufa; Wong, Terrence; Lemal, David M. Journal of Fluorine Chemistry, 2006 , vol. 127, # 6 p. 688 - 703

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Citation Number: 4

Abstract

cis-1, 2, 3, 4, 5, 5-Hexafluorobicyclo [2.1. 0] pentane and 1, 2, 4, 5-tetrafluorobicyclo [2.1. 0] pentane have been synthesized from hexafluorobenzene. The former hydrofluorocarbon, which exists entirely in the endo configuration, rearranges to cis-1, 2, 3, 3, 4, 5- hexafluorocyclopentene below room temperature (Ea= 21.9 kcal/mol, logA= 13.4). The latter undergoes degenerate ring inversion with extraordinary ease (ΔG‡= 6.8±0.2 kcal/mol at− ...