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Title

Unusual behaviour of thermally generated oxygen 1,3-diradicals from β-peroxylactones: stereoselective synthesis of a tetrahydrofuran ring by intramolecular hydrogen abstraction

AuthorsHernández, Rosendo CSIC; Marrero, José J.; Suárez, Ernesto CSIC ORCID
Issue Date1990
PublisherRoyal Society of Chemistry (UK)
CitationChemical Communications 1990(7): 524-526 (1990)
AbstractThermolysis of the steroidal β-peroxylactone (3) gave ether (4), produced by intramolecular hydrogen abstraction from a non-activated carbon; the reaction occurs with complete stereoselectivity by abstraction of the C7-pro-R hydrogen, and a concerted mechanism is proposed, no free radicals seem to be involved in the reaction since when a true free radical hydrogen abstraction was realized with alcohol (7) no selectivity was observed and a mixture of ethers (4) and (8) was obtained.
Description3 pages, 1 figure, 1 table, 1 scheme.
Publisher version (URL)http://dx.doi.org/10.1039/C39900000524
URIhttp://hdl.handle.net/10261/16427
DOI10.1039/C39900000524
ISSN1359-7345
Appears in Collections:(IPNA) Artículos

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