Ultrasound assisted remote functionalization of non-activated carbon atoms: eff...

• Author(s): Costa, Saul C. P. ; Moreno, M. J. S. Miranda ; Melo, M. Luísa Sá e ; Neves, André S. Campos
• Date: 1999
• Persistent ID: http://hdl.handle.net/10316/5815
• Origin: Estudo Geral - Universidade de Coimbra
• Subject(s): steroids; tetrahydrofurans; halohydrins; sonochemistry
• Document Type: Article
• Language: English

Description

Ultrasonic irradiation of bromohydrins in the presence of (diacetoxyiodo)benzene and I2 generates alkoxyl radicals which lead in situ to intramolecular hydrogen abstraction on the C-19 non-activated carbon atoms in steroids producing tetrahydrofurans selectively in very good yields. Photolysis was less effective in promoting such conversions. http://www.sciencedirect.com/science/article/B6THS-3YF4638-1R/1/f44fcc813a57c32b99eaa2f5bc98b937