Please use this identifier to cite or link to this item: http://hdl.handle.net/10261/17259
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Title

Fragmentation of alkoxy radicals: Tandem β-fragmentation-cycloperoxyiodination reaction

AuthorsBoto, Alicia CSIC ORCID ; Betancor, Carmen; Prangé, Thierry; Suárez, Ernesto CSIC ORCID
Issue DateAug-1994
PublisherAmerican Chemical Society
CitationJournal of Organic Chemistry 59(16): 4393-4401 (1994)
AbstractThe steroidal alcohols 2-cholesten-5α-ol (3), 3-phenyl-2-cholesten-5α-ol (4) , and 3αH-2'-oxofuro-[2,3]cholestan-5α-ol (5) were prepared in order to test a new tandem β-fragmentation-cycloperoxyiodination reaction. The alkoxy radicals generated by irradiation of these alcohols with visible light in the presence of (diacetoxyiodo)benzene, I2, and molecular oxygen undergo a β-fragmentation reaction with subsequent peroxidation of the C-radical formed. This peroxy radical is added to conveniently positioned double bonds to give 10-membered cyclic ketones possessing a 1,2-dioxolane group.
Description9 pages, 1 table, 9 schemes.-- Supplementary material available: 1H NMR spectra of compounds 4,5,7-16,17-23 and 25-29, 1H NMR of compounds 16 and 24, and ORTEP drawing from the X-ray analysis of compound 21 (49 pages).
Publisher version (URL)http://dx.doi.org/10.1021/jo00095a012
URIhttp://hdl.handle.net/10261/17259
DOI10.1021/jo00095a012
ISSN0022-3263
Appears in Collections:(IPNA) Artículos

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