A rearrangement in the reaction of 2-bromomethyl-1,3-thiaselenole with ethanol: synthesis of 2-ethoxy-2,3-dihydro-1,4-thiaselenine

摘要

We are carrying out systematic investigations aimed at introduction of novel reagents such as selenium dichloride and dibromide into organic synthesis. The reaction of selenium dihalides with divinyl sulfide leads to 2,6-di-halo-1,4-thiaselenanes. When kept in chloroform solution at room temperature, 2,6-dihalo-1,4-thiaselenanes undergo spontaneous rearrangement with ring contraction to 5-halo-2-halomethyl-1,3-thiaselenolanes. 2-Halomethyl-1,3-thiaselenoles were obtained by de-hydrohalogenation reaction of 5-halo-2-halomethyl-1,3-thiaselenolanes in high yields.