Reacción #514077

ord-0185a1f20f56408bb293b00c80eec266

Ecuación de reacción

O=[N+]([O-])c1ccc(S(=O)(=O)[O-])c([N+](=O)[O-])c1.[Na+]
sodium 2,4-dinitrobenzenesulfonate
O=C(O)c1cc([N+](=O)[O-])cc([N+](=O)[O-])c1
3,5-dinitrobenzoic acid
→
C=CS(=O)(=O)CS(=O)(=O)C=C
bis(vinylsulfonyl)methane
Rendimiento 85.0%

Reactantes

O=[N+]([O-])c1ccc(S(=O)(=O)[O-])c([N+](=O)[O-])c1.[Na+]
sodium 2,4-dinitrobenzenesulfonate
O=C(O)c1cc([N+](=O)[O-])cc([N+](=O)[O-])c1
3,5-dinitrobenzoic acid

Reactivos

Ninguno

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Procedimiento

By the procedure used in A, except that sodium 2,4-dinitrobenzenesulfonate was substituted for 3,5-dinitrobenzoic acid, a 16.5 g (85 percent yield) sample (m.p. 59°-61° C.) of bis(vinylsulfonyl)methane was obtained. A 2 percent by weight aqueous solution was made up (no insoluble material) and let stand for more than 10 months at room temperature. Analysis of the still clear solution by high pressure liquid chromatography (HPLC) showed a 1.6 percent concentration of bis(vinylsulfonyl)methane remaining. A sample of the dry compound was also kept at room temperature for more than 10 months. A fresh 2 percent by weight solution made from this sample was found to contain 1.8 percent bis(vinylsulfonyl)methane by HPLC analysis.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US04171976uspto-grants-1979_10