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Title

Steroidal N-nitroamines. Part 4. Intramolecular functionalization of N-nitroamine radicals: synthesis of 1,4-nitroimine compounds

AuthorsArmas, Pedro de ; Francisco, Cosme G. ; Hernández, Rosendo ; Salazar, José A.; Suárez, Ernesto
Issue Date1988
PublisherRoyal Society of Chemistry (UK)
CitationJournal of the Chemical Society - Perkin Transactions 1988(12): 3255-3265 (1988)
AbstractPhotolysis of 6β-nitroamino-5α-cholestane (4), 6β-nitroamino-5α-cholestan-3β-yl-acetate (5), 2β-nitroamino-5α-cholestane (13), 4β-nitroamino-5α-cholestane (17), (20R)-20-nitroaminopregn-5-en-3β-yl acetate (26), (20R)-(31) and (20S)-(34)-nitroamino-5α-pregnan-3β-yl acetate, (23R, 25S)-3β-acetoxy-23-nitroamino-5β-spirostan (46), 3β-nitroaminofriedelane (53), and methyl 3β-nitroaminofriedelan-29-oate (54) in the presence of iodine and various oxidative reagents leads to neutral nitroaminyl radicals which undergo intramolecular hydrogen-abstraction to produce in most cases N-nitroimine compounds. Best results were obtained with the system iodine and (diacetoxyiodo) benzene.
Description10 pages, 1 figure, 1 table, 3 schemes.
Publisher version (URL)http://dx.doi.org/10.1039/P19880003255
URIhttp://hdl.handle.net/10261/16411
DOI10.1039/P19880003255
ISSN1472-7781
Appears in Collections:(IPNA) Artículos
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