Addition of selenium dibromide to divinyl sulfide: spontaneous rearrangement of 2,6-dibromo-1,4-thiaselenane to 5-bromo-2-bromomethyl-1,3-thiaselenolane

作者：Amosova Svetlana V; Penzik Maxim V; Albanov Alexander I; Potapov Vladimir A

来源：Tetrahedron Letters, 2009, 50(3): 306-308.

DOI：10.1016/j.tetlet.2008.10.148

Synthesis of the novel selenium heterocycles 1, 2, and 3 based on the addition reaction of selenium dibromide to divinyl sulfide is described. The reaction proceeded in CCl(4) at room temperature to give the thia-selenane 1. Even at low temperature in chloroform solution, the 6-membered thiaselenane 1 underwent spontaneous rearrangement to the 5-membered thiaselenolane 2. In turn, the thiaselenolane 2 underwent spontaneous dehydrobromination to the thiaselenole 3 in chloroform.

• 出版日期2009-1-21