9-Methoxyisocolchicide 1 in excess methanethiolate–methanol, or Me2SO, slowly undergoes ipso-substitution giving 9-methylthioisocolchicide 3, which then suffers tele-substitution giving 11-methylthioisocolchicide 2; this activation by dicoordinated sulfur is used for amino re-functionalisation of the isocolchicide system.
M. Cavazza and F. Pietra, J. Chem. Soc., Chem. Commun., 1994, 897 DOI: 10.1039/C39940000897
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