Nils Henning Nilsson

Studies of electron-depleted thiocarbonyl compounds—IV : Reactions of trithiocarbonate S,S-dioxides with 1,3-dienes and with tetramethylallene☆

Abstract The trithioorthocarboxylate S,S-dioxides B, a new class of compounds, can be conveniently prepared from trithiocarbonate S,S-dioxides 1 either by Diels-Alder reaction with suitable 1,3-dienes or by ene reaction with tetramethylallene. The monocyclic Diels-Alder adducts 4 readily lose sulfinic acid to yield the 2H-thiopyrans 5, while treatment of 4 with catalytic amounts of acid results in rearrangement to the isomeric Δ2-dihydrothiopyrans 6.