Novel synthesis of α-nitroalkenes from nitroalkanes via halogenation of intermediate N,N-bis(silyloxy)enamines

Novel synthesis of α-nitroalkenes from nitroalkanes via halogenation of intermediate N,N-bis(silyloxy)enamines Full article

Journal

Tetrahedron Letters
ISSN: 0040-4039 , E-ISSN: 1873-3581

Output data

Year: 2005, Volume: 46, Number: 31, Pages: 5203-5205 Pages count : 3 DOI: 10.1016/j.tetlet.2005.05.113

Authors

Kunetsky Roman A. ¹ , Dilman Alexander D. ¹ , Struchkova Marina I. ¹ , Tartakovsky Vladimir A. ¹ , Ioffe Sema L. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, 119991 Moscow, Leninsky prosp. 47, Russian Federation

An approach to conjugated nitroalkenes via oxidation of N,N-bis(silyloxy)enamines with bromine or iodine in the presence of tetra-n-butylammonium acetate is described. The acetate ion plays a key role by acting as a mild desilylating reagent. This new strategy allows the synthesis of α-nitroalkenes from the corresponding nitroalkanes.

Kunetsky R.A. , Dilman A.D. , Struchkova M.I. , Tartakovsky V.A. , Ioffe S.L.
Novel synthesis of α-nitroalkenes from nitroalkanes via halogenation of intermediate N,N-bis(silyloxy)enamines
Tetrahedron Letters. 2005. V.46. N31. P.5203-5205. DOI: 10.1016/j.tetlet.2005.05.113 WOS Scopus OpenAlex

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