ELECTROSYNTHESIS OF NEW STEREOISOMERS OF ALKYLTHIO AND ARYLTHIO DERIVATIVES OF LEVOGLUCOSENONE

Cathodically initiated Michael addition of thiols to levoglucosenone using small currents produces the previously unknown threo addition product in several instances. The normal erythro isomer, identified as the kinetic product, tends to be formed when large currents are used. The slow, low current electrolyses promote equilibration of the two forms so that erythro can be converted to three by the retro reaction and readdition. Additions to R-(+)-apoverbenone and R-(-)-carvone are also reported.