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Please use this identifier to cite or link to this item: http://dspace.library.iitb.ac.in/jspui/handle/10054/5475

Title: ALLYLIC ACETOXYLATION OF DELTA-5-STEROIDS - OBSERVATION OF A COMPETING PATHWAY - A C-13-NMR STUDY OF 5-BETA-BROMO STEROIDS
Authors: DESAI, UR
BAIG, MHA
TRIVEDI, GK
Keywords: neighboring group participation
nuclear magnetic-resonance
2-dimensional spectroscopy
oxidation
Issue Date: 1991
Publisher: COUNCIL SCIENTIFIC INDUSTRIAL RESEARCH
Citation: INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 30(12), 1085-1088
Abstract: The allylic acetoxylation of (25R)-spirost-5-en-22-alpha-O-3-beta-yl-acetate (1) using bromine/silver acetate/pyridine/-60-degrees has been studied. Besides the expected 4-actoxy derivative 2 (72%), two products in minor amounts, viz. 5-beta, 6-alpha-dibromo-3-beta-acetoxy steroid (3, 12%) and 5-beta-bromo-3-beta,6-beta-diacetoxy steroid (4, 4%) are obtained. The isolation of products 3 and 4 indicate a competing reaction pathway, albeit in small manner. The C-13 NMR spectra of 5-beta-bromo steroids are studied. Influence of bromine on gamma-carbons, the gamma-g effect, is found to be of immense help in deducing the A/B cis-fusion as well as to highlight configurational and conformational factors.
URI: http://dspace.library.iitb.ac.in/xmlui/handle/10054/5475
http://hdl.handle.net/10054/5475
ISSN: 0376-4699
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