Novel Keto-Enol Systems: Cyclobutane Derivatives

PE Lindner, RA Correa, J Gino…

Index: Lindner, Patrick E.; Correa, Ricardo A.; Gino, James; Lemal, David M. Journal of the American Chemical Society, 1996 , vol. 118, # 11 p. 2556 - 2563

Full Text: HTML

Citation Number: 21

Abstract

3 H-Perfluorobicyclo [2.2. 0] hexan-2-one (3) has been synthesized from hexafluorobenzene and equilibrated with its enol form (4). In carbon tetrachloride K e/k= 0.07±0.01 (25° C), but in Lewis basic solvents (eg acetonitrile, ether, and tetrahydrofuran) only enol is detectable at equilibrium because of its strength as a hydrogen bond donor. In the monocyclic counterpart of this keto-enol system, 2 H-perfluorocyclobutanone (1) and perfluorocyclobut-1-enol (2), ...