ELECTROSYNTHESIS OF NEW STEREOISOMERS OF ALKYLTHIO AND ARYLTHIO DERIVATIVES OF LEVOGLUCOSENONE

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