反应详情

Trimethylsulphonium iodide (9.8 g, 0.048 moles) was dissolved in water (50 ml). Sulphuric acid (4.8 g at 98%, 0.048 moles) and hydrogen peroxide (2.72 g at 30%. 0.024 moles) were each diluted to 10 ml with water and added to the stirred trimethylsulphonium iodide solution. Carbon tetrachloride (150 ml) was added to extract the iodine that was produced and the mixture was stirred for 6 hours. The layers were separated. To the aqueous layer was added carbon tetrachloride (150 ml) and this was stirred overnight. The layers were separated and the aqueous layer was extracted with aliquots of carbon tetrachloride (20 ml) until no further pink colouration was visible. Palladium on carbon (3%, 0.25 g) was added to the aqueous solution to destroy any unreacted peroxide. The solution was filtered after 60 minutes, and washed with ether (2×20 ml). The water was removed under reduced pressure to produce an oily residue which was dried under vacuum at 780° C. The oil was dissolved in hot ethanol and cooled in an acetone/solid carbon dioxide bath to produce a white solid. The solid was filtered off, maintaining the temperature below 0° C. and dried under reduced pressure at 78° C. to yield a very deliquescent residue (2.7 g, 32% yield of theory). This material was dissolved in hot ethanol and allowed to cool slowly in an acetone/solid carbon dioxide bath to produce a waxy solid. The solid was filtered off, maintaining the temperature below 0° C. and dried under reduced pressure at 80° C. to yield a very deliquescent residue, melting point 20°-21° C. C3H10S2O4 (174.2): calculated C 20.7, H 5.8, S 36.8; found C 20.7, H 5.9, S 36.6. 1H NMR (DMSO-D6 /TMS): & 2.91(s, 9H, CH3 --S); 7.4-7.6(s, 1H, HSO4). pH=1.8-1.9 (HSO4-).

1. extractionto extract the iodine that
2. customwas produced
3. customThe layers were separated
4. additionTo the aqueous layer was added carbon tetrachloride (150 ml)
5. stirringthis was stirred overnight
6. customThe layers were separated
7. extractionthe aqueous layer was extracted with aliquots of carbon tetrachloride (20 ml) until no further pink colouration
8. additionPalladium on carbon (3%, 0.25 g) was added to the aqueous solution
9. customto destroy any unreacted peroxide
10. filtrationThe solution was filtered after 60 minutes
11. washwashed with ether (2×20 ml)
12. customThe water was removed under reduced pressure
13. customto produce an oily residue which
14. customwas dried under vacuum at 780° C
15. dissolutionThe oil was dissolved in hot ethanol
16. temperaturecooled in an acetone/solid carbon dioxide bath
17. customto produce a white solid
18. filtrationThe solid was filtered off
19. temperaturemaintaining the temperature below 0° C.
20. customdried under reduced pressure at 78° C.
21. customto yield a very deliquescent residue (2.7 g, 32% yield of theory)
22. temperatureto cool slowly in an acetone/solid carbon dioxide bath
23. customto produce a waxy solid
24. filtrationThe solid was filtered off
25. temperaturemaintaining the temperature below 0° C.
26. customdried under reduced pressure at 80° C.
27. customto yield a very deliquescent residue, melting point 20°-21° C