Aerobic radical multifunctionalization of alkenes using tert-butyl nitrite and water

Water induces a change in the product of radical multifunctionalization reactions of aliphatic alkenes involving an sp(3) C–H functionalization by an 1,5-hydrogen shift using tert-butyl nitrite and molecular oxygen. The reaction without water, reported previously, gives nitrated γ-lactols, whereas t...

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Detalles Bibliográficos
Autores principales: Hirose, Daisuke, Taniguchi, Tsuyoshi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2013
Materias:
Letter
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3778400/
https://www.ncbi.nlm.nih.gov/pubmed/24062832
http://dx.doi.org/10.3762/bjoc.9.196
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author Hirose, Daisuke
Taniguchi, Tsuyoshi
author_facet Hirose, Daisuke
Taniguchi, Tsuyoshi
author_sort Hirose, Daisuke
collection PubMed
description Water induces a change in the product of radical multifunctionalization reactions of aliphatic alkenes involving an sp(3) C–H functionalization by an 1,5-hydrogen shift using tert-butyl nitrite and molecular oxygen. The reaction without water, reported previously, gives nitrated γ-lactols, whereas the reaction in the presence of water produces 4-hydroxy-5-nitropentyl nitrate or 4-hydroxy-3-nitropentyl nitrate derivatives.
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spelling pubmed-37784002013-09-23 Aerobic radical multifunctionalization of alkenes using tert-butyl nitrite and water Hirose, Daisuke Taniguchi, Tsuyoshi Beilstein J Org Chem Letter Water induces a change in the product of radical multifunctionalization reactions of aliphatic alkenes involving an sp(3) C–H functionalization by an 1,5-hydrogen shift using tert-butyl nitrite and molecular oxygen. The reaction without water, reported previously, gives nitrated γ-lactols, whereas the reaction in the presence of water produces 4-hydroxy-5-nitropentyl nitrate or 4-hydroxy-3-nitropentyl nitrate derivatives. Beilstein-Institut 2013-08-20 /pmc/articles/PMC3778400/ /pubmed/24062832 http://dx.doi.org/10.3762/bjoc.9.196 Text en Copyright © 2013, Hirose and Taniguchi https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Letter
Hirose, Daisuke
Taniguchi, Tsuyoshi
Aerobic radical multifunctionalization of alkenes using tert-butyl nitrite and water
title Aerobic radical multifunctionalization of alkenes using tert-butyl nitrite and water
title_full Aerobic radical multifunctionalization of alkenes using tert-butyl nitrite and water
title_fullStr Aerobic radical multifunctionalization of alkenes using tert-butyl nitrite and water
title_full_unstemmed Aerobic radical multifunctionalization of alkenes using tert-butyl nitrite and water
title_short Aerobic radical multifunctionalization of alkenes using tert-butyl nitrite and water
title_sort aerobic radical multifunctionalization of alkenes using tert-butyl nitrite and water
topic Letter
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3778400/
https://www.ncbi.nlm.nih.gov/pubmed/24062832
http://dx.doi.org/10.3762/bjoc.9.196
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AT taniguchitsuyoshi aerobicradicalmultifunctionalizationofalkenesusingtertbutylnitriteandwater

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