Categories: S-S Bond Formation >
Synthesis of Trisulfides
A convenient synthesis of unsymmetrical trisulfides using 9-fluorenylmethyl (Fm) disulfides as the precursors provides the desired products in good yields under mild conditions.
S. Xu, Y. Wang, M. N. Radford, A. J. Ferrell, M. Xian, Org. Lett., 2018, 20, 465-468.
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.
D. Ali, R. Hunter, C. H. Kaschula, S. De Doncker, S. C. M. Rees-Jones, J. Org. Chem., 2019, 84, 2862-2869.
A straightforward preparation of 1-[(5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinan-2-yl)trisulfanyl]dodecane from readily available substrates, followed by reaction with aliphatic and aromatic thiols enables the synthesis of unsymmetrical trisulfides under mild conditions in very good yields.
S. Lach, M. Sliwka-Kaszynska, D. Witt, Synlett, 2010, 2857-2860.
Convenient methods for the synthesis of symmetrical trisulfides from aliphatic and aromatic thiols under mild conditions are based on the straightforward preparation of (5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorin-2-yl)disulfanyl derivatives from readily available 5,5-dimethyl-2-sulfanyl-2-thioxo-1,3,2-dioxaphosphorinane or bis(5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinan-2-yl) disulfide.
A. Kertmen, S. Lach, J. Rachon, D. Witt, Synthesis, 2009, 1459-1462.