Ultrasound assisted remote functionalization of non-activated carbon atoms:: efficient in situ formation of tetrahydrofurans by sonolysis of bromohydrins with (diacetoxyiodo)benzene/I2

[摘要] Ultrasonic irradiation of bromohydrins in the presence of (diacetoxyiodo)benzene and It 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. (C) 1999 Elsevier Science Ltd. All rights reserved.

[发布日期] 1999-12-03

[关键词] steroids;tetrahydrofurans;halohydrins;sonochemistry