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

TETRAHEDRON LETTERS

卷:40

Article

Costa, SCP ; Moreno, MJSM ; Melo, MLSE ; Neves, ASC

关键词: steroids;    tetrahydrofurans;    halohydrins;    sonochemistry;   

DOI  :  10.1016/S0040-4039(99)01849-3

来源: Elsevier

【 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.

【 授权许可】

Free