SYNTHESIS OF 2-HETEROSUBSTITUTED 1,3-OXATHIANES AND THEIR REACTION WITH sec-BUTILLITHIUM

Article abstract of DOI:10.1016/S0040-4039(01)92890-4

A series of 2-heterosubstituted 1,3-oxathianes were synthesized and their reactivity toward a strong base, sec-butyllithium, was studied.It was shown that sec-butyllithium attacked 2-heterosubstituted 1,3-oxathianes in three different ways depending upon the heteroatom at C-2; the removal of the proton at C-2, the nucleophilic attack at heteroatom, or the nucleophilic attack at C-2 took place.