Selenosilane-Promoted Selective Mild Transformation of N-Thiophthalimides into Symmetric Disulfides
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The reactivity of N-thiophthalimides with silyl chalcogenides is described. Treatment of N-thiophthalimides with bis(trimethylsilyl) sulfide [(Me3Si)2S] leads to the formation of a mixture of the corresponding disulfides and trisulfides. On the other hand, N-thiophthalimides react with bis(trimethylsilyl) selenide [(Me3Si)2Se] under TBAF catalysis to smoothly give variously substituted diaryl, divinyl, and dialkyl disulfides; formation of a selenotrisulfide (dithiaselane, RSSeSR) is rationalized as an intermediate. Exploiting the different chemical behavior of silyl chalcogenides, we have disclosed a novel, selective, and operationally simple method to access disulfides in good yields under mild conditions.
2019 ◽
Vol 39
(2)
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pp. 403-422
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1916 ◽
Vol 62
(258)
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pp. 556-572
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2021 ◽
Vol 922
(1)
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pp. 012007
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1999 ◽
Vol 173
◽
pp. 249-254
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1969 ◽
Vol 27
◽
pp. 6-7
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