Synthesis, Table of Contents Synthesis 2019; 51(08): 1819-1824DOI: 10.1055/s-0037-1610354 paper © Georg Thieme Verlag Stuttgart · New York Selenosilane-Promoted Selective Mild Transformation of N-Thiophthalimides into Symmetric Disulfides Caterina Viglianisi , Chiara Bonardi , Elena Ermini , Antonella Capperucci , Stefano Menichetti , Damiano Tanini * Dipartimento di Chimica ‘Ugo Schiff’, Via della Lastruccia 3-13, 50019 Sesto Fiorentino (FI), Italy Email: damiano.tanini@unifi.it › Author Affiliations Recommend Article Abstract Buy Article All articles of this category Abstract 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. Key words Key wordsdisulfides - selenosilane - N-thiophthalimides - trisulfides - selenium - sulfur Full Text References References For selected reports, see: 1a Musiejuk M, Witt D. Org. Prep. Proced. Int. 2015; 47: 95 1b Mandal B, Basu B. RSC Adv. 2014; 4: 13854 1c Kondo T, Mitsudo T. Chem. Rev. 2000; 100: 3205 1d Metzner P, Thuillier A. Sulfur Reagents in Organic Synthesis . Katritzky AR. Academic Press; San Diego: 1994 2a Xiao X, Xue J, Jiang X. Nat. Commun. 2018; 9: 2191 2b Block E. 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