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Issue 12, 2019
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Synthesis, structural characterisation, and synthetic application of stable seleniranium ions

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Abstract

Stable seleniranium ions were prepared from easily available stable bromiranium ions and diselenides. The solid state structure of the obtained seleniranium ions was determined by X-ray crystallographic analysis and their alkene-to-alkene transfer was investigated by NMR techniques. The rapid alkene-to-alkene transfer of the selenium group enabled the application of the seleniranium ion salts as selenenylating agents, which led to very efficient and highly diastereoselective, selenium-induced polyene-type cyclisations of terpene analogues.

Graphical abstract: Synthesis, structural characterisation, and synthetic application of stable seleniranium ions

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Article information


Submitted
11 Jan 2019
Accepted
26 Feb 2019
First published
26 Feb 2019

Org. Biomol. Chem., 2019,17, 3181-3185
Article type
Paper

Synthesis, structural characterisation, and synthetic application of stable seleniranium ions

J. Bock, C. G. Daniliuc, K. Bergander, C. Mück-Lichtenfeld and U. Hennecke, Org. Biomol. Chem., 2019, 17, 3181
DOI: 10.1039/C9OB00078J

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