A General Metal‐Assisted Synthesis of α‐Halo Oxime Ethers from Nitronates and Nitro Compounds

A General Metal‐Assisted Synthesis of α‐Halo Oxime Ethers from Nitronates and Nitro Compounds Full article

Journal

European Journal of Organic Chemistry
ISSN: 1434-193X , E-ISSN: 1099-0690

Output data

Year: 2014, Volume: 2014, Number: 36, Pages: 8148-8159 Pages count : 12 DOI: 10.1002/ejoc.201403083

Authors

Sukhorukov Alexey Yu. ¹ , Kapatsyna Maria A. ² , Yi Tammy Lim Ting ³ , Park Hyeong Ryool ³ , Naumovich Yana A. ² , Zhmurov Petr A. ¹ , Khomutova Yulia A. ¹ , Ioffe Sema L. ^4,1 , Tartakovsky Vladimir A. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Leninsky prospect 47, 119991 Moscow, Russia, http://www.ioc.ac.ru/
2	D. Mendeleev University of Chemical Technology of Russia, Miusskaya square 9, 125047 Moscow, Russia
3	National Junior College, Hillcrest Road 37, 288913 Singapore, Singapore
4	Moscow Chemical Lyceum, Tamozhenniy proezd 4, 111033 Moscow, Russia

An approach to the synthesis of α-halo oxime ethers from readily accessible nitronates and nitro compounds via bis(oxy)enamines is reported. A key step of the strategy involves the unprecedented reaction of bis(oxy)enamines with a metal (Co, Zn, Mg, Mn) halide that acts as both a promoter and halide (Br, I, Cl) source. A variety of cyclic and acyclic ethers of α-halo oximes, including previously unavailable trimethylsilyl ethers of α-iodo oximes, have been synthesized in good-to-high yields.

Sukhorukov A.Y. , Kapatsyna M.A. , Yi T.L.T. , Park H.R. , Naumovich Y.A. , Zhmurov P.A. , Khomutova Y.A. , Ioffe S.L. , Tartakovsky V.A.
A General Metal‐Assisted Synthesis of α‐Halo Oxime Ethers from Nitronates and Nitro Compounds
European Journal of Organic Chemistry. 2014. V.2014. N36. P.8148-8159. DOI: 10.1002/ejoc.201403083 WOS Scopus OpenAlex

Web of science:	WOS:000346161500021
Scopus:	2-s2.0-84917690767
OpenAlex:	W1523738553

DB	Citing
OpenAlex	20
Scopus	21
Web of science	20