Preparation of pentafluorosulfanyl (SF5) pyrrole carboxylic acid esters.
Pyrrole derivatives bearing a pentafluorosulfanyl group are currently unknown. In this paper, a facile preparation of SF5-substituted pyrrole carboxylic acid esters in good yield is reported. Utilizing the cycloaddition of an azomethine ylide to pentafluorosulfanylalkynes, a series of dihydropyrroles were prepared and oxidized to the respective 1-tert-butyl-4-(pentafluorosulfanyl)pyrrole-2-carboxylic acid esters in good yield. Further treatment of these pyrroles with catalytic triflic acid allowed removal of the tert-butyl group.
Dolbier
William R
WR
Department of Chemistry, University of Florida, PO Box 117200, Gainesville, Florida 32611-7200, USA. wrd@chem.ufl.edu
Zheng
Zhaoyun
Z
D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D015394:Molecular Structure; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D002264:Carboxylic Acids; D011758:Pyrroles