Record number :
Title of article :
Chlorosulfonation of 2-acylthiophenes: an examination on the reaction regiochemistry
Author/Authors :
Arduini، نويسنده , , Arturo and Pochini، نويسنده , , Andrea and Secchi، نويسنده , , Andrea and Ugozzoli، نويسنده , , Franco، نويسنده ,
Issue Information :
هفته نامه با شماره پیاپی سال 2003
Pages :
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Abstract :
Chlorosulfonation of thenoyltrifluoroacetone with neat chlorosulfuric acid was found to give a 25:75 mixture of 3- and 2-chlorosulfonated thenoyltrifluoroacetone isomers in 33% overall yield. The use of dichloromethane as solvent for the chlorosulfonation reaction gave only the 2-chlorosulfonated isomer in 45% yield. On the contrary, the reaction of 2-acetylthiophene with neat chlorosulfuric acid gave only the 3-chlorosulfonated-5-acetylthiophene in 35% yield. The identity of these chlorosulfonated compounds was unambiguously established by NMR techniques and confirmed by the crystal structure determination of the 2-chlorosulfonated isomer.
Keywords :
Thiophenes , chlorosulfonation , Heterocyclic compounds
Journal title :
Tetrahedron Letters
Serial Year :
Link To Document :