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).
P. Hamel, Y. Girard and J. G. Atkinson, J. Chem. Soc., Chem. Commun., 1989, 63 DOI: 10.1039/C39890000063
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