Regioselectivity in 2-X-pyrazine aminations by O-mesitylenesulfonylhydroxylamine

Regioselectivity in 2-X-pyrazine aminations by O-mesitylenesulfonylhydroxylamine Full article

Journal

Tetrahedron Letters
ISSN: 0040-4039

Output data

Year: 2009, Volume: 50, Number: 49, Pages: 6779-6782 Pages count : DOI: 10.1016/j.tetlet.2009.09.103

Tags

Amination; Selectivity; N-Amine salts; Azines; Mechanism; Linear free energy relationship; DFT calculations

Authors

Borodkin Gennady I. ^1,2 , Vorob'ev Aleksey Yu. ^1,2 , Shakirov Makhmut M. ¹ , Shubin Vyacheslav G. ¹

Affiliations

1	(Данные Web of science) Vorozhtsov Novosibirsk Inst Organ Chem, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Univ, Novosibirsk 630090, Russia

The regioselectivity of 2-X-pyrazine aminations by O-mesitylenesulfonylhydroxylamine was studied experimentally and the results are discussed from the viewpoint of electronic and steric factors. DFT calculations are consistent with the reaction proceeding according to an S(N)2 mechanism. (C) 2009 Elsevier Ltd. All rights reserved.

Borodkin G.I. , Vorob'ev A.Y. , Shakirov M.M. , Shubin V.G.
Regioselectivity in 2-X-pyrazine aminations by O-mesitylenesulfonylhydroxylamine
Tetrahedron Letters. 2009. V.50. N49. P.6779-6782. DOI: 10.1016/j.tetlet.2009.09.103 WOS Scopus РИНЦ

Published print:

Dec 1, 2009

Web of science	WOS:000271603000012
Scopus	2-s2.0-70350020767
Elibrary	15305659
OpenAlex	W2021054321