Ultrasound assisted remote functionalization of non-activated carbon atoms: efficient in situ formation of tetrahydrofurans by sonolysis of bromohydrins with (diacetoxyiodo)benzene/I-2

Authors
Costa, SCP Moreno, MJSM Melo, MLSE Neves, ASC
Citation
Scp. Costa et al., Ultrasound assisted remote functionalization of non-activated carbon atoms: efficient in situ formation of tetrahydrofurans by sonolysis of bromohydrins with (diacetoxyiodo)benzene/I-2, TETRAHEDR L, 40(49), 1999, pp. 8711-8714
Citations number
15
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
49
Year of publication
1999
Pages
8711 - 8714
Database
ISI
SICI code
0040-4039(199912)40:49<8711:UARFON>2.0.ZU;2-P
Abstract
Ultrasonic irradiation of bromohydrins in the presence of (diacetoxyiodo)be nzene and It generates alkoxyl radicals which lead in situ to intramolecula r hydrogen abstraction on the C-19 non-activated carbon atoms in steroids p roducing tetrahydrofurans selectively in very good yields. Photolysis was l ess effective in promoting such conversions. (C) 1999 Elsevier Science Ltd. All rights reserved.