Michael Addition of P-Nucleophiles to Conjugated Nitrosoalkenes

Michael Addition of P-Nucleophiles to Conjugated Nitrosoalkenes Full article

Journal

Journal of Organic Chemistry
ISSN: 1520-6904 , E-ISSN: 0022-3263

Output data

Year: 2019, Volume: 84, Number: 11, Pages: 7244-7254 Pages count : 11 DOI: 10.1021/acs.joc.9b00924

Authors

Naumovich Yana A. ¹ , Ioffe Sema L. ¹ , Sukhorukov Alexey Yu. ^2,1,3

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Leninsky Prospect, 47, Moscow 119991, Russia
2	Higher Chemical College, D. Mendeleev University of Chemical Technology of Russia, Miusskaya sq., 9, Moscow 125047, Russia
3	Plekhanov Russian University of Economics, Stremyanny per. 36, Moscow 117997, Russia

A general approach to various α-phosphorus-substituted oximes (β-oximinoalkyl-substituted phosphonates, phosphine oxides, phosphine–borane complexes, and phosphonium salts) was developed. The strategy exploits hitherto unknown Michael addition of PH-containing compounds (diphenylphosphine oxide, diisopropyl phosphite, phosphine–borane complexes, and triphenylphosphonium bromide) to unstable conjugated nitrosoalkenes, which are generated in situ from corresponding nitrosoacetals. The resulting α-phosphorus-substituted oximes can be considered as useful P-, N-, and O-ligands for catalysis and precursors to valuable β-aminophosphonates.

Naumovich Y.A. , Ioffe S.L. , Sukhorukov A.Y.
Michael Addition of P-Nucleophiles to Conjugated Nitrosoalkenes
Journal of Organic Chemistry. 2019. V.84. N11. P.7244-7254. DOI: 10.1021/acs.joc.9b00924 WOS Scopus OpenAlex

Web of science:	WOS:000471212000064
Scopus:	2-s2.0-85066940366
OpenAlex:	W2943899691

DB	Citing
OpenAlex	11
Scopus	12
Web of science	9