Michael addition of amines to sterically crowded ortho-benzoquinone completed with unprecedented 1,2-shift of a tert-butyl group

A strong electron-withdrawing nitro group introduced into the 6-position of 3,5-di-(tert-butyl)-1,2-benzoquinone provides for activation of the sterically blocked Michael addition reaction channel. Addition of amines to the quinone is followed by a concerted 1,2-migration of a tert-butyl group to af...

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Asıl Yazarlar:	Demidov, O. P., Демидов, О. П.
Materyal Türü:	Статья
Dil:	English
Baskı/Yayın Bilgisi:	Elsevier Ltd 2021
Konular:	6-Nitrocyclohexa-2,5-dienones Density functional calculations alkyl 1,2-migration Michael addition Quinones
Online Erişim:	https://dspace.ncfu.ru/handle/20.500.12258/14784
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id	ir-20.500.12258-14784
record_format	dspace
spelling	ir-20.500.12258-147842021-12-01T10:06:11Z Michael addition of amines to sterically crowded ortho-benzoquinone completed with unprecedented 1,2-shift of a tert-butyl group Demidov, O. P. Демидов, О. П. 6-Nitrocyclohexa-2,5-dienones Density functional calculations alkyl 1,2-migration Michael addition Quinones A strong electron-withdrawing nitro group introduced into the 6-position of 3,5-di-(tert-butyl)-1,2-benzoquinone provides for activation of the sterically blocked Michael addition reaction channel. Addition of amines to the quinone is followed by a concerted 1,2-migration of a tert-butyl group to afford derivatives of 4-amino-3-nitrocyclohexa-3,5-diene-1,2-dione system. The multistep reaction mechanism was examined using DFT computational methods 2021-01-21T14:16:14Z 2021-01-21T14:16:14Z 2021 Статья Ivakhnenko, E., Malay, V., Romanenko, G., Demidov, O., Knyazev, P., Starikov, A., Minkin, V. Michael addition of amines to sterically crowded ortho-benzoquinone completed with unprecedented 1,2-shift of a tert-butyl group // Tetrahedron. - 2021. - Volume 79. - Номер статьи 131841 http://hdl.handle.net/20.500.12258/14784 en Tetrahedron application/pdf application/pdf Elsevier Ltd
institution	СКФУ
collection	Репозиторий
language	English
topic	6-Nitrocyclohexa-2,5-dienones Density functional calculations alkyl 1,2-migration Michael addition Quinones
spellingShingle	6-Nitrocyclohexa-2,5-dienones Density functional calculations alkyl 1,2-migration Michael addition Quinones Demidov, O. P. Демидов, О. П. Michael addition of amines to sterically crowded ortho-benzoquinone completed with unprecedented 1,2-shift of a tert-butyl group
description	A strong electron-withdrawing nitro group introduced into the 6-position of 3,5-di-(tert-butyl)-1,2-benzoquinone provides for activation of the sterically blocked Michael addition reaction channel. Addition of amines to the quinone is followed by a concerted 1,2-migration of a tert-butyl group to afford derivatives of 4-amino-3-nitrocyclohexa-3,5-diene-1,2-dione system. The multistep reaction mechanism was examined using DFT computational methods
format	Статья
author	Demidov, O. P. Демидов, О. П.
author_facet	Demidov, O. P. Демидов, О. П.
author_sort	Demidov, O. P.
title	Michael addition of amines to sterically crowded ortho-benzoquinone completed with unprecedented 1,2-shift of a tert-butyl group
title_short	Michael addition of amines to sterically crowded ortho-benzoquinone completed with unprecedented 1,2-shift of a tert-butyl group
title_full	Michael addition of amines to sterically crowded ortho-benzoquinone completed with unprecedented 1,2-shift of a tert-butyl group
title_fullStr	Michael addition of amines to sterically crowded ortho-benzoquinone completed with unprecedented 1,2-shift of a tert-butyl group
title_full_unstemmed	Michael addition of amines to sterically crowded ortho-benzoquinone completed with unprecedented 1,2-shift of a tert-butyl group
title_sort	michael addition of amines to sterically crowded ortho-benzoquinone completed with unprecedented 1,2-shift of a tert-butyl group
publisher	Elsevier Ltd
publishDate	2021
url	https://dspace.ncfu.ru/handle/20.500.12258/14784
work_keys_str_mv	AT demidovop michaeladditionofaminestostericallycrowdedorthobenzoquinonecompletedwithunprecedented12shiftofatertbutylgroup AT demidovop michaeladditionofaminestostericallycrowdedorthobenzoquinonecompletedwithunprecedented12shiftofatertbutylgroup
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Michael addition of amines to sterically crowded ortho-benzoquinone completed with unprecedented 1,2-shift of a tert-butyl group

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