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Synthesis 2016; 48(01): 57-64
DOI: 10.1055/s-0035-1560348
DOI: 10.1055/s-0035-1560348
paper
Ammonium Iodide Catalyzed Selenolactonization of Unsaturated Acids
Further Information
Publication History
Received: 26 June 2015
Accepted after revision: 05 September 2015
Publication Date:
24 September 2015 (online)
Abstract
A convenient procedure is developed for the preparation of selenolactones from unsaturated acids and diselenides using a catalytic amount of ammonium iodide in combination with m-chloroperoxybenzoic acid as the oxidant. This catalytic ring-closing method proceeds efficiently at room temperature under neutral conditions, and in short reaction times, to afford the corresponding selenolactones in good yields. Using the same reaction conditions, cyclic selenoethers and tellurocyclization products are prepared, thus extending the catalytic application of inorganic iodides in organic synthesis.
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