β,β′-functionalized N,N-divinyl-N-trimethylsilyloxyamines via silylation of β-substituted aliphatic nitro compounds. The investigation of the mechanism of the process using selective trapping reagents

Autor:	Alexander A. Tishkov, Vitaliy M. Danilenko, Vladimir A. Tartakovsky, Yu. A. Strelenko, Ilya M. Lyapkalo, Sema L. Ioffe
Rok vydání:	1997
Předmět:	Acrylate Trimethylsilyl Silylation Organic Chemistry Trapping Biochemistry Medicinal chemistry chemistry.chemical_compound chemistry Reagent Drug Discovery Ethyl vinyl ether Nitro Acetamide
Zdroj:	Tetrahedron. 53:13085-13098
ISSN:	0040-4020
Popis:	Hitherto unknown N,N-divinyl-N-trimethylsilyloxyamines of the general formula [XC(R)=ch]2NOSiMe3 (X = CO2Me. CN. 5-methyloxycarbonylisoxazolin-3-yl; R = H, Me, CH(Me)CO2Me) were obtained with moderate to good yields by silylation of nitro compounds XCH(R)CH2NO2 with N,O-bis(trimethylsilyl)acetamide. The mechanism of this reaction was studied by the example of silylation of methyl-3-nitropropionate using selective trapping reagents. Trimethylsilyl ester of the starting aci-nitro compound and methyl 2-nitroso acrylate were intercepted as consecutive intermediates. Thus, the silylation of β-functionalized nitro compounds could be presented as a convenient route to practically unknown β-substituted nitroso-alkenes XC(R)=CHNO which behave as active 1,3-heterodienes towards ethyl vinyl ether used as trapping reagent.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::dc480a61f2dd97be3bb4919da73f6bd5 https://doi.org/10.1016/s0040-4020(97)00831-4 Zobrazit plný text záznamu Full Text from ScienceDirect