Bis(trimethylsilyl)selenide in the Selective Synthesis of β‐Hydroxy, β‐Mercapto, and β‐Amino Diorganyl Diselenides and Selenides Through Ring Opening of Strained Heterocycles. Issue 2 (21st November 2014)

• Record Type: Journal Article
• Authors: Tanini, Damiano; Degl'Innocenti, Alessandro; Capperucci, Antonella
• Is Part Of: European journal of organic chemistry. Issue 2(2015)
• Page Start: 357
• Page End: 369
• Publication Date: 2014-11-21
• Subjects: Synthetic methods -- Small ring systems -- Strained molecules -- Selenium -- Regioselectivity; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201403015
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: A novel approach to the synthesis of β‐substituted dialkyl diselenides and selenides is described through reaction of bis(trimethylsilyl)selenide with epoxides, thiiranes, and aziridines catalyzed by tetrabutylammonium fluoride. Selective formation of a wide variety of β‐hydroxy, β‐mercapto, and β‐amino diselenides and selenides is achieved by controlling the reaction conditions in the regioselective attack of the silyl selenide onto the ring‐strained heterocycles. All reactions occur in a highly regioselective and enantioconservative manner, affording the title compounds with good to high yields. Selenium‐77 NMR chemical shifts were measured to verify the selective formation of the β‐substituted diselenides and selenides. Abstract : A selective approach to β‐hydroxy, β‐mercapto, and β‐amino dialkyl diselenides and selenides is described through reaction of bis(trimethylsilyl)selenide (HMDSS) with epoxides, thiiranes, and aziridines under suitable reaction conditions. 77 Se NMR chemical shifts were measured to verify the selective synthesis of diselenides and selenides.