Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
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Reduction of Acetals with Samarium Diiodide in Acetonitrile in the Presence of Lewis Acids
Munetaka KUNISHIMADaisuke NAKATATakayuki SAKUMAKazuhiro KONOShoichi SATOShohei TANI
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2001 年 49 巻 1 号 p. 97-100

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Transformation of acetals into ethers by partial reduction using a samarium diiodide—Lewis acids—acetonitrile system is described. The reaction with aromatic acetals occurred in good yields in the presence of aluminum chloride (2 eq) whereas the corresponding aliphatic, vinylic, and alkynyl derivatives did not afford ethers under the same conditions. β-Elimination to give an enol ether becomes predominant when aliphatic acetals that possess a hydrogen at the 2-position are treated with iodotrimethylsilane in the presence of SmI2 or SmI3.
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© 2001 The Pharmaceutical Society of Japan
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