毛子的期刊,how old,恐怕当时还是毛子语的,不好弄
Chlorides of N-arylsulfonylaryleneaminosulfonic acids
Levchenko, E. S.; Derkach, N. Ya.; Kirsanov, A. V.
Zhurnal Obshchei Khimii (1960), 30, 1971-5 CODEN: ZOKHA4; ISSN: 0044-460X.
cf. CA 55, 3484g. Slowly adding 0.05 mole powdered ArSO2NNaCl to 0.05 mole Ar'SOCl in 80 ml. C6H6 and refluxing 1-1.5 hrs. gave, after filtration and evaporation, a solid residue of Ar'SO(:NSO2Ar)Cl (Ar', Ar, % yield, and melting point given): Ph, Ph, 57, 93-4°; Ph, p-MeC6H4, 76, 73-4°; Ph, p-MeOC6H4, 93, 76-8°; Ph, p-ClC6H4, 55, 110-11°; Ph, p-O2NC6H4, 73, 129-30°; Ph, 2-C10H7, 51, 89-91°; p-MeC6H4, Ph, 65, 94-5°; p-MeC6H4, p-MeC6H4, 78, 76-8°; p-MeC6H4, p-MeOC6H4, 91, 121-2°; p-MeC6H4, p-ClC6H4, 98, 89-90°; p-MeC6H4, p-O2NC6H4, 73, 138-9°; p-MeC6H4, 2-C10H7, 63, 113-15°. These compds. were most soluble in CHCl3 or C6H6, with lesser solubility in Et2O, hexane, and petr. ether. Kinetic curves were given for the hydrolysis of these substances in hot H2O, aqueous MeOH-NaOH, aqueous alc. HCl, and aqueous Me2CO. Hydrolysis with H2O was a zero order reaction at 100°. Alkalies in aqueous EtOH converted these chlorides to [Ar'SO2NSO2Ar] Na, which (on acidification) yielded Ar'SO2NHSO2Ar (Ar, Ar', and melting point given): Ph, Ph, 157-8°; Ph, p-MeC6H4, 169-71°; Ph, p-MeOC6H4, 149-51°; Ph, p-ClC6H4, 177-9°; Ph, p-O2NC6H4, 168-70°; Ph, 2-C10H7, 143-5°; p-MeC6H4, p-MeC6H4, 171-3°; p-MeC6H4, p-MeOC6H4, 153-4°; p-MeC6H4, p-ClC6H4, 161-3°; p-MeC6H4, p-O2NC6H4, 198-200°; p-MeC6H4, 2-C10H7, 142-4°. Hydrolysis in acid medium also yielded these imides, but the reaction tended to proceed beyond them to sulfonamides as well; under mild conditions, the yield of imides was about 80%, and that of sulfonamides about 10%. The following rate constants were determined for hydrolysis at 50° in 1:1 aqueous Me2CO for PhSO(:NSO2Ar)Cl (Ar shown): Ph, 8.1 × 10-3/minimum; p-tolyl, 7.5 × 10-3; p-anisyl, 10.0 × 10-3; p-ClC6H4, 8.4 × 10-3; p-O2NC6H4, 8.7 × 10-3; 2-naphthyl, 92 × 10-3. The reaction was 1st order. |