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

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

3 pages, 1 figure, 1 table, 1 scheme.

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Bibliographic Details
Main Authors: Hernández, Rosendo, Marrero, José J., Suárez, Ernesto
Other Authors: Dirección General de Investigación Científica y Técnica, DGICT (España)
Format: artículo biblioteca
Language:English
Published: Royal Society of Chemistry (UK) 1990
Online Access:http://hdl.handle.net/10261/16427
http://dx.doi.org/10.13039/501100008737
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spelling dig-ipna-es-10261-164272014-03-03T09:34:44Z Unusual behaviour of thermally generated oxygen 1,3-diradicals from β-peroxylactones: stereoselective synthesis of a tetrahydrofuran ring by intramolecular hydrogen abstraction Hernández, Rosendo Marrero, José J. Suárez, Ernesto Dirección General de Investigación Científica y Técnica, DGICT (España) Ministerio de Educación y Ciencia (España) 3 pages, 1 figure, 1 table, 1 scheme. Thermolysis 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. This work was supported by the Investigation Programme No. PB0406 of the Dirección General de Investigación Científica y Técnica. J.J.M. thanks the Ministerio de Educación y Ciencia, Spain, for a fellowship. 2009-08-31T08:00:40Z 2009-08-31T08:00:40Z 1990 artículo http://purl.org/coar/resource_type/c_6501 Chemical Communications 1990(7): 524-526 (1990) 1359-7345 http://hdl.handle.net/10261/16427 10.1039/C39900000524 http://dx.doi.org/10.13039/501100008737 en http://dx.doi.org/10.1039/C39900000524 none 2373 bytes 298790 bytes text/plain application/pdf Royal Society of Chemistry (UK)
institution IPNA ES
collection DSpace
country España
countrycode ES
component Bibliográfico
access En linea
databasecode dig-ipna-es
tag biblioteca
region Europa del Sur
libraryname Biblioteca del IPNA España
language English
description 3 pages, 1 figure, 1 table, 1 scheme.
author2 Dirección General de Investigación Científica y Técnica, DGICT (España)
author_facet Dirección General de Investigación Científica y Técnica, DGICT (España)
Hernández, Rosendo
Marrero, José J.
Suárez, Ernesto
format artículo
author Hernández, Rosendo
Marrero, José J.
Suárez, Ernesto
spellingShingle Hernández, Rosendo
Marrero, José J.
Suárez, Ernesto
Unusual behaviour of thermally generated oxygen 1,3-diradicals from β-peroxylactones: stereoselective synthesis of a tetrahydrofuran ring by intramolecular hydrogen abstraction
author_sort Hernández, Rosendo
title Unusual behaviour of thermally generated oxygen 1,3-diradicals from β-peroxylactones: stereoselective synthesis of a tetrahydrofuran ring by intramolecular hydrogen abstraction
title_short Unusual behaviour of thermally generated oxygen 1,3-diradicals from β-peroxylactones: stereoselective synthesis of a tetrahydrofuran ring by intramolecular hydrogen abstraction
title_full Unusual behaviour of thermally generated oxygen 1,3-diradicals from β-peroxylactones: stereoselective synthesis of a tetrahydrofuran ring by intramolecular hydrogen abstraction
title_fullStr Unusual behaviour of thermally generated oxygen 1,3-diradicals from β-peroxylactones: stereoselective synthesis of a tetrahydrofuran ring by intramolecular hydrogen abstraction
title_full_unstemmed Unusual behaviour of thermally generated oxygen 1,3-diradicals from β-peroxylactones: stereoselective synthesis of a tetrahydrofuran ring by intramolecular hydrogen abstraction
title_sort unusual behaviour of thermally generated oxygen 1,3-diradicals from β-peroxylactones: stereoselective synthesis of a tetrahydrofuran ring by intramolecular hydrogen abstraction
publisher Royal Society of Chemistry (UK)
publishDate 1990
url http://hdl.handle.net/10261/16427
http://dx.doi.org/10.13039/501100008737
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AT marrerojosej unusualbehaviourofthermallygeneratedoxygen13diradicalsfrombperoxylactonesstereoselectivesynthesisofatetrahydrofuranringbyintramolecularhydrogenabstraction
AT suarezernesto unusualbehaviourofthermallygeneratedoxygen13diradicalsfrombperoxylactonesstereoselectivesynthesisofatetrahydrofuranringbyintramolecularhydrogenabstraction
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