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Chemistry of 1,3-Dioxepins. XIII. (E)/(Z) Configurational Assignment of 4,7-Dihydro-4-hydroxyimino-6-nitro-1,3-dioxepins

Milena Jadrijević-Mladar Takač ; Department of Pharmaceutical Chemistry, Faculty of Pharmacy and Biochemistry University of Zagreb, A. Kovačića 1, HR–10000 Zagreb, Croatia
Ivan Butula ; Department of Pharmaceutical Chemistry, Faculty of Pharmacy and Biochemistry University of Zagreb, A. Kovačića 1, HR–10000 Zagreb, Croatia
Dražen Vikić-Topić ; Ruđer Bošković Institute, NMR Center, Bijenička cesta 54, HR–10001 Zagreb, Croatia
Miljenko Dumić ; PLIVA–Research Institute, Prilaz baruna Filipovića 25, HR–10000 Zagreb, Croatia


Puni tekst: engleski pdf 113 Kb

str. 557-571

preuzimanja: 249

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Sažetak

The configuration of oximes 1a and 1b was investigated by chemical and spectroscopic methods. Under the Beckmann rearrangement conditions, using sulfonyl chlorides as reagents, the sulfonic esters 2a-c were obtained. Under more drastic conditions, using PCl5 or P2O5, the only isolated product was 4-nitro-5H-furan-2-on (3). It was also formed as the sole product by hydrolysis of oximes 1a-b, as well as sulfonic ester 2a. The structure of all compounds was determined by one- and twodimensional homo- and hetero-nuclear 1H and 13C NMR correlated 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.

Ključne riječi

Hrčak ID:

132367

URI

https://hrcak.srce.hr/132367

Datum izdavanja:

1.10.1998.

Posjeta: 599 *