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Unsymmetrical Organotrisulfide Formation via Low-Temperature Disulfanyl Anion Transfer to an Organothiosulfonate

Doaa Ali, Roger Hunter*, Catherine H. Kaschula, Stephen De Doncker, Sophie C. M. Rees-Jones

*Department of Chemistry, University of Cape Town, Rondebosch 7701, South Africa, Email:

D. Ali, R. Hunter, C. H. Kaschula, S. De Doncker, S. C. M. Rees-Jones, J. Org. Chem., 2019, 84, 2862-2869.

DOI: 10.1021/acs.joc.8b03262

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A low-temperature deprotection of disulfanyl acetates with sodium methoxide in THF provides disulfanyl anions, which react rapidly in situ with organothiosulfonates within 30 seconds followed by quenching. Using this efficient method, a range of organotrisulfides covering aliphatic, aromatic, as well as cysteine and sugar groups can be accessed in a high yield and purity.

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Key Words


ID: J42-Y2019