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

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

Journal

Tetrahedron
ISSN: 0040-4020

Output data

Year: 2021, Volume: 79, Article number : 131841, Pages count : 6 DOI: 10.1016/j.tet.2020.131841

Tags

Michael addition, Quinones, Density functional calculations alkyl 1,2-migration, 6-Nitrocyclohexa-2,5-dienones

Authors

Ivakhnenko Eugeny ¹ , Malay Vasily ¹ , Romanenko Galina ² , Demidov Oleg ³ , Knyazev Pavel ¹ , Starikov Andrey ¹ , Minkin Vladimir ¹

Affiliations

1	Institute of Physical and Organic Chemistry, Southern Federal University, 194/2 Stachki St., Rostov-on-Don, 344091, Russian Federation
2	International Tomography Center, Siberian Branch of Russian Academy of Sciences, 3a Institutskaya St., Novosibirsk, 630090, Russian Federation
3	North Caucasus Federal University, 1 Pushkin St., Stavropol, 355017, Russian Federation

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.

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. V.79. 131841 :1-6. DOI: 10.1016/j.tet.2020.131841 WOS Scopus

Published print:

Jan 21, 2021

Web of science:	WOS:000604923900016
Scopus:	2-s2.0-85097794196

DB	Citing
Scopus	2
Web of science	2