Thia-Fries rearrangement of aryl sulfonates in dry media under microwave activation

Tetrahedron Letters

Volumn 41, Issue 18, 2000, Pages 3479-3481

  Moghaddam, Firouz Matloubi ^a   Dakamin, Mohammad G ^a  

^a SHARIF UNIVERSITY OF TECHNOLOGY   (Iran)

Author keywords

Aryl sulfonates; Dry media; Microwave irradiation; Thia Fries rearrangement

Indexed keywords

ALUMINUM CHLORIDE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SULFONIC ACID DERIVATIVE; ZINC CHLORIDE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; HEAT TREATMENT; MICROWAVE RADIATION; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0034728930     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00402-0     Document Type: Article

References (19)

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14. The support was prepared as described in Ref. 7 and the minimum amount of supported reagent to substrate was found to be 3:1 (w/w) after performing several optimization experiments. General procedure for thia-Fries rearrangement of sulfonates: To a solution of arylsulfonate (1 g) in 5 ml of anhydrous chloroform, 3 g of support was added. After evaporation of the solvent, the mixture was subjected to microwave irradiation for the given times (Table 1). The cooled reaction mixture was extracted with ethyl acetate (3×50 ml) and the solvent was evaporated under vacuum. The product was isolated by column chromatography of the crude reaction mixture on silica gel (eluent: dichloromethane:petroleum ether).
15. The microwave oven used for this work was an AEG (650 Watt) at 2450 MHz (100% power) which was modified to a focused monomode system in our laboratory.
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