Addition of selenium dibromide to divinyl sulfide: spontaneous rearrangement of 2,6-dibromo-1,4-thiaselenane to 5-bromo-2-bromomethyl-1,3-thiaselenolane
摘要:
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 CCl4 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. (C) 2008 Elsevier Ltd. All Fights reserved.
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:Svetlana V. Amosova、Maxim V. Penzik、Alexander I. Albanov、Vladimir A. Potapov
DOI:10.1016/j.tetlet.2008.10.148
日期:2009.1
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 CCl4 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. (C) 2008 Elsevier Ltd. All Fights reserved.