Acid-catalyzed isomerization of 3-indolyl sulfides to 2-indolyl sulfides: first synthesis of 3-unsubstituted 2-arylthioindoles. Evidence for a complex intermolecular …

P Hamel, Y Girard, JG Atkinson

Index: Hamel, Pierre; Girard, Yves; Atkinson, Joseph G. Journal of Organic Chemistry, 1992 , vol. 57, # 9 p. 2694 - 2699

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Citation Number: 30

Abstract

The acid-catalyzed isomerization of 3-indolyl sulfides 1 to the corresponding 2-indolyl sulfides 4 provides the fit synthesis of 3-unsubstituted 2-(arylthio) indoles, a hitherto unattainable class of compounds. When catalyzed by trifluoroacetic acid, the isomerization proceeds mainly via an intermolecular mechanism involving initial disproportionation to a 2, 3-indolyl bis-sulfide 5 and an unsubstituted counterpart 6 followed by further interaction of ...