M. Rahman, B. Secor, K. Morgan
Aug 1, 1990
Citations
0
Influential Citations
11
Citations
Journal
Journal of the American Chemical Society
Abstract
Three interconverting 1,2,3,4,5,6-hexafluorocycloocta-1,3,5-triene/bicyclo [4.2.0] octa-2,4-diene systems have been synthesized (unsubstituted (2), cis-difluoro-substituted (3), and fully fluorinated (4) at the methylene carbons). Equilibrium constants, plus enthalpy and entropy changes for 2 and 3, have been measured for these valence isomerizations. For cyclization of 4 the equilibrium constant is about 4300 times that of 2. The equilibrium constant for cyclization of octafluorocyclooctatetraene to its bicyclic isomer is also reported, and comparisons are drawn between various quantities measured in this work and their counterparts in hydrocarbon systems. Implications of some of our findings for the strain energy content of octafluorocyclobutane are discussed