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Preparation of 3,4-di-t-butylthiophene 1-imide and itsN-substituted derivatives

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
41
Issue
44
Identifiers
DOI: 10.1016/s0040-4039(00)01481-7
Keywords
  • Thiophenes
  • Sulfimides/Sulfilimines
  • Sulfonium Salts

Abstract

Abstract Treatment of 3,4-di- t-butylthiophene 1-oxide with (CF 3CO) 2O or (CF 3SO 2) 2O, followed by reaction with RSO 2NH 2, ROC(O)NH 2, or RCONH 2 furnished a series of 1-imino derivatives of 3,4-di- t-butylthiophene, which carry an electron-withdrawing substituent on the imino nitrogen atom. Treatment of an imino derivative (substituent on the nitrogen atom=CO 2 t Bu) with CF 3CO 2H gave the corresponding aminosulfonium salt, whose deprotonation led to the N-unsubstituted parent 1-imide derivative.

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