Selective synthesis of 4-thiomethyl-1,3-dioxolan-2-ones under microwave irradiation using an environmentally benign KF/Al2O3/PEG-400 system

Rongalite®/PEG-400 as reducing system in the synthesis of new glycerol-derived selenol esters using anhydrides and bis-(2,2-dimethyl-1,3-dioxolanylmethyl)diselenide as substrates

“…In this sense, five-membered cyclic ketals, which are synthesized by the reaction of the terminal and central hydroxyl groups of the glycerol with a ketone, have many applications, especially their use as an additive for fuels and solvents, and as intermediates in pharmaceutical industry. 42 In recent years, our group have reported new derivatizations of such ketals, including the preparation of chalcogen-containing analogs of solketal, like 4-thiomethyl-1,3-dioxolan-2-ones, 43 vinyl-or alkynyl chalcogenides 44 and enantiomerically pure bis-(2,2-dimethyl-1,3-dioxolanylmethyl)chalcogenides and dichalcogenides. 45 As a continuation of our studies on the utilization of the glycerol-derivative bis-(2,2-dimethyl-1,3-dioxolanylmethyl)diselenide 44 1 in organic synthesis, we present here our results on the reaction of diselenide 1 with anhydrides 2a-h for the synthesis of selenol esters 3a-h by a clean method, using Rongalite® (sodium hydroxymethanesulfinate dihydrate, HOCH 2 SO 2 Na) 46 in the presence of a base and using PEG-400 as green solvent (Scheme 1).…”