Trimethylsilyl Nitronates Derived from 2-Substituted Nitroethanes in δ-Elimination Reactions
Silylation of β-substituted nitroethanes XCH2CH2NO2 (X=Cl or OCOCH3) with conventional silylating agents yields corresponding trimethylsilyl nitronates which undergo δ-elimination of nitroethylene under the reaction conditions.Stable silyl nitronates containing one or two trimethylsilyl groups were isolated in the silylation of C6H5NHCH2CH2NO2. 1,3-Dipolar cycloaddition of the nitronates to methoxide ion results in formation of 5-methoxycarbonyl-3-phenylaminomethyl(or 3-N-trimethylsilylphenylaminomethyl)-3-trimethylsiloxyisoxazolidines.Thermolysis of the latter affords 5-methoxycarbonyl-2-isoxazoline.
Ioffe, S. L.,Makarenkova, L. M.,Strelenko, Yu. A.,Tartakovskii, V. A.
