Issue 12, 2019

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

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

Supplementary files

Article information

Article type
Paper
Submitted
11 Jan 2019
Accepted
26 Feb 2019
First published
26 Feb 2019

Org. Biomol. Chem., 2019,17, 3181-3185

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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