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: Roger.Hunter
uct.ac.za
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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Abstract
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
