The complete and irreversible conversion of a cis carbon-substituted thiiranium ion into the trans isomer
Abstract
t-2-tert-Butyl-t-3-phenyl-r-1-methylthiiranium 1 isomerizes into the more stable (32.3 kJ mol–1) t-2-tert-butyl-c-3-phenyl-r-1-methylthiiranium 2 in a complete and irreversible process (monitored by proton NMR at –30 °C) via an open benzylic carbenium ion.