Trimethylsilylsulfonyl chloride as a source of sulfur trioxide: A novel synthesis of sultones

Tetrahedron Letters

Volumn 40, Issue 41, 1999, Pages 7417-7420

  Bassindale, Alan R ^a   Katampe, Ibrahim ^a   Maesano, Maria G ^a   Patel, Pravin ^a   Taylor, Peter G ^a  

^a OPEN UNIVERSITY   (United Kingdom)

Author keywords

Alkenes; Hypervalent elements; Silicon halides; Sultones

Indexed keywords

ALKENE; BENZENE DERIVATIVE; CHLORINE DERIVATIVE; SULFUR DERIVATIVE; SULTONE;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033536667     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01450-1     Document Type: Article

References (17)

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11. 11. Synthesis of sultones: To a slurry of iodosobenzene (2.20 g, 0.01 mol) in 50 ml dry dichloromethane, at -78°C under nitrogen atmosphere was added chlorotrimethylsilylsulfonate ester (1.5 ml, 0.01 mol) with continuous stirring to produce a clear yellow solution. To this was added the alkene (1.5 g, 0.015 mol), and the reaction mixture allowed to warm up to room temperature. Stirring was continued at this temperature for a further 1 h, followed by removal of the solvent from the reaction mixture. Purification of the crude product using column chromatography (silica gel with hexane/dichloromethane as the eluent) gave the sultones in the yields quoted in Table 1.
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16. 3: C 64.6, H 4.7; found: C 65.0, H 4.9.
17. 3: C 44.4, H 6.2; found: C 44.7, H 6.1.