Chemistry of 1, 3-dioxepines. XIII. (E)/(Z) Configurational Assignment of 4, 7-Dihydro-4- hydroxyimino-6-nitro-1, 3-dioxepins (CROSBI ID 211499)
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Jadrijević-Mladar Takač, Milena ; Butula, Ivan ; Vikić-Topić, Dražen ; Dumić, Miljenko
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Chemistry of 1, 3-dioxepines. XIII. (E)/(Z) Configurational Assignment of 4, 7-Dihydro-4- hydroxyimino-6-nitro-1, 3-dioxepins
The configuration of oximes 1a and 1b was investigated by chemical and spectroscopic methods. Under the Beckmann rearrangement conditions, using sulfonyl chlorides as reagent, the sulfonic esters 2a-c were obtained. Under more drastic condition, using PCl5 or P2O5, the only isolated product was 4-nitro-5H-furan-2-on (3). It was also formed as sole product by hydrolysis of oximes 1a-b, as well as sulfonic ester 2a. The structure of all compounds were determined by one- and two-dimensional homo- and heteronuclear 1H and 13C NMR correlation spectra: COSY, NOESY, HETCOR and HMBC. Gradient selected differential NOE measurements confirmed that in dimethylsulfoxide solution oximes 1a and 1b exist in E-configuration, irrespective of the route of their formation.
1; 3-Dioxepins; 4; 7-Dihydro-4-hydroxyimino-6-nitro-1; 3-dioxepins; (E)/(Z) Configurational assignment; 1D and 2D NMR spectra; 1H and 13C NMR correlated spectra; Differential NOE
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