Acid-catalysed isomerization of indol-3-yl sulphides to indol-2-yl sulphides: unexpected intermolecular nature of the rearrangement

P Hamel, Y Girard, JG Atkinson

Index: Hamel, Pierre; Girard, Yves; Atkinson, Joseph G. Journal of the Chemical Society, Chemical Communications, 1989 , # 1 p. 63 - 65

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Citation Number: 3513

Abstract

The rearrangement of indol-3-yl sulphides (1) to indol-2-yl sulphides (4), catalysed by proton acids, unexpectedly proceeds by an intermolecualr mechanism involving initial disproportionation to an indole-2, 3-diyl bis-sulphide (2) and an indole (3), followed by a reaction between (2) and (3) to yield the rearranged product (4).