Collect. Czech. Chem. Commun. 1987, 52, 199-206

Sulphonates and carboxylates of (E)- and (Z)-3-(hydroxymethylene)-trans-hexahydro-2(3H)-benzofuranone

Ctibor Mazal and Jaroslav Jonas

Department of Organic Chemistry, Faculty of Natural Sciences, University J. E. Purkyně, 611 37 Brno


Sodium salt of 3-(hydroxymethylene)-trans-hexahydro-2(3H)-benzofuranone has been found to be formed as the (Z)-isomer in solid state and to exist as the (E)-isomer or a mixture of the both isomers in polar solvents. Some sulphonates and carboxylates of (E)-3-(hydroxymethylene)-trans-hexahydro-2(3H)-benzofuranone and (Z)-3-(hydroxymethylene)-trans-hexahydro-2(3H)-benzofuranone have been prepared by reactions of the corresponding isomers of this sodium salt with sulphonyl and acyl chlorides, respectively. The configuration of the isomeric derivatives was confirmed by 1H and 13C NMR spectra.