The sily-durst chlorination of hydroxy sulfoxides

Tetrahedron Letters

Volumn 38, Issue 25, 1997, Pages 4407-4410

  Oddon, G ^a   Uguen, D ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

[No Author keywords available]

Indexed keywords

SULFONE DERIVATIVE; SULFOXIDE;

ARTICLE; CHEMICAL REACTION; CHLORINATION; ENANTIOMER; REACTION ANALYSIS;

EID: 0030950921     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00942-8     Document Type: Article

References (7)

1. Breuilles, P.; Schmittberger, T.; Uguen, D. Tetrahedron Lett. 1993, 34, 4205-4208.
2. Durst, T.; Tin, K.-C.; Marcil, M. J. V. Can. J. Chem. 1973, 51, 1704-1712.
3. The sulfone 1d, which also formed (ca 4%), was eliminated by column chromatography (hexane/AcOEt).
4. D values have been measured at 21°C.
5. 1H NMR spectra. equation presented.
6. The small amount of sulfone 7 (ca 10%), which still formed, was easily eliminated by flash-chromatography on silica gel (hexane/AcOEt). On a larger scale (5-10 g), trace amount of the isomeric chlorosulfone 1b was detected (NMR).
7. 2, in presence of triethylamine (1.2 eq.) and DMAP (0.2 eq.), the work-up consisting in the evaporation of solvents, followed by filtration of the residue on a short column of silica gel (AcOEt).