Diorganodichalcogenides and their intramolecular cyclization reactions

作者：Poellnitz Alpar; Silvestru Anca^*

来源：Tetrahedron, 2015, 71(19): 2914-2921.

DOI：10.1016/j.tet.2015.03.058

• Diorganodichalcogenides
• Benzo[b]chalcogenophenes
• Condensation reaction
• Intramolecular cyclization

Bis(2-acetylphenyl)dichalcogenides of type [2-(O=CMe)C6H4](2)E-2 (E=S, Se, Te) were prepared by the hydrolysis of [2-{(CH2O)(2)C(CH3)}C6H4](2)E-2. In their reaction with benzylamine these species yield an air-sensitive condensation product, which undergoes a fast, unexpected oxidative intramolecular cyclization. This process proved to be a very convenient way to prepare 3-amino substituted benzo[b]chalcogenophenes. By contrast, the reaction between [2-(O=CMe)C6H4]TeCl and benzylamine resulted in the condensation product [2-(C6H4CH2N=CMe)C6R4]TeCl.

• 出版日期2015-5-13