K. Bott, ALKYLATION REACTIONS BY MEANS OF ALKANOLS AND CARBON-MONOXIDE - AN EFFICIENT SYNTHESIS OF THIOETHERS AND OF CAFFEINE FROM THEOPHYLLINE, Chemische Berichte, 126(8), 1993, pp. 1955-1956
The reaction of sodium or potassium thialates with alkanols and carbon
monoxide provides a versatile route to produce thioethers in excellen
t yields. By analogy, the potassium salt of theophylline suffers a nea
rly quantitative conversion to caffeine when heated with methanol unde
r CO pressure. The mechanism of these alkylation reactions is discusse
d.