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 sp3 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...

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Main Authors:	Daisuke Hirose, Tsuyoshi Taniguchi
Format:	Article
Language:	English
Published:	Beilstein-Institut 2013-08-01
Series:	Beilstein Journal of Organic Chemistry
Subjects:	C−H oxidation free radical nitration oxygen radicals water
Online Access:	https://doi.org/10.3762/bjoc.9.196

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spelling	doaj-251cf208a1124533b7486fc8232f05f22021-02-02T05:01:15ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972013-08-01911713171710.3762/bjoc.9.1961860-5397-9-196Aerobic radical multifunctionalization of alkenes using tert-butyl nitrite and waterDaisuke Hirose0Tsuyoshi Taniguchi1Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan,School of Pharmaceutical Sciences, Institute of Medical, Pharmaceutical and Health Sciences, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, JapanWater induces a change in the product of radical multifunctionalization reactions of aliphatic alkenes involving an sp3 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.https://doi.org/10.3762/bjoc.9.196C−H oxidationfree radicalnitrationoxygenradicalswater
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Daisuke Hirose Tsuyoshi Taniguchi
spellingShingle	Daisuke Hirose Tsuyoshi Taniguchi Aerobic radical multifunctionalization of alkenes using tert-butyl nitrite and water Beilstein Journal of Organic Chemistry C−H oxidation free radical nitration oxygen radicals water
author_facet	Daisuke Hirose Tsuyoshi Taniguchi
author_sort	Daisuke Hirose
title	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_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_sort	aerobic radical multifunctionalization of alkenes using tert-butyl nitrite and water
publisher	Beilstein-Institut
series	Beilstein Journal of Organic Chemistry
issn	1860-5397
publishDate	2013-08-01
description	Water induces a change in the product of radical multifunctionalization reactions of aliphatic alkenes involving an sp3 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.
topic	C−H oxidation free radical nitration oxygen radicals water
url	https://doi.org/10.3762/bjoc.9.196
work_keys_str_mv	AT daisukehirose aerobicradicalmultifunctionalizationofalkenesusingtertbutylnitriteandwater AT tsuyoshitaniguchi aerobicradicalmultifunctionalizationofalkenesusingtertbutylnitriteandwater
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Aerobic radical multifunctionalization of alkenes using tert-butyl nitrite and water

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