Isomerization and Cleavage of Allyl Ethers of Carbohydrates by Trans- [Pd(NH3)2Cl2
作者:
Tadeusz Bieg,
Wieslaw Szeja,
期刊:
Journal of Carbohydrate Chemistry
(Taylor Available online 1985)
卷期:
Volume 4,
issue 3
页码: 441-446
ISSN:0732-8303
年代: 1985
DOI:10.1080/07328308508070194
出版商: Taylor & Francis Group
数据来源: Taylor
摘要:
Allyl ethers are widely used for the “temporary” protection of hydroxy groups in carbohydrates. The allyl group is conveniently removed by isomerization and subsequent cleavage of the labile prop-1-enyl group.2The rearrangement of allyl ethers to prop-1-enyl ethers is readily achieved by treatment with potassium t-butoxide in dimethyl sulfoxide, using tris(tripheny1phosphine)rhodium chloride, palladium on activated charcoal and by an ene reaction with diethylazodicarboxylate. acidic conditions, ozonolysis followed by alkaline hydrolysis, reaction with alkaline permanganate solution, or treatment with mercuric chloride in the presence of mercuric oxide. The isomerization of allyl ethers to prop-1-enyl ethers can also be carried out in the presence of palladium on carbon or complex bis(benzonitrile)palladium(11) chloride. Bruce and Roshan-Ali' showed that derivatives of allyl phenyl ether are smoothly cleaved by this complex. This has made it possible to remove the protecting group in a one-pot operation. We have now investigated the effect of palladium catalysts on the isomerization and cleavage of the allyl group in carbohydrate derivatives.
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