Synthesis 2019; 51(08): 1819-1824
DOI: 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
,
Dipartimento di Chimica ‘Ugo Schiff’, Via della Lastruccia 3-13, 50019 Sesto Fiorentino (FI), Italy   Email: damiano.tanini@unifi.it
› Author Affiliations
Further Information

Publication History

Received: 22 October 2018

Accepted after revision: 13 November 2018

Publication Date:
07 January 2019 (online)


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.

Supporting Information

 
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