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Oxydations et halogénations régiosélectives et réactions carbéniques de dérivés de sucres portant un groupement thioéther

 

作者: Jean M. J. Tronchet,   Hansjörg Eder,  

 

期刊: Helvetica Chimica Acta  (WILEY Available online 1980)
卷期: Volume 63, issue 1  

页码: 16-28

 

ISSN:0018-019X

 

年代: 1980

 

DOI:10.1002/hlca.19800630104

 

出版商: WILEY‐VCH Verlag GmbH

 

数据来源: WILEY

 

摘要:

Regioselective Oxidations, Regioselective Halogenations and Carbene Reactions of Sugar Derivatives Bearing a Thioether GroupRegioselective stoechiometrically controlled procedures are described for the oxidation of thiosugars either at the sulfur atom (to sulfoxides or sulfones) or at a hydroxymethylene group (to ketosugars). Ruthenium tetraoxide reacted at both sites. Chloration (SO2Cl2) of β‐ketothioether sugar derivative3took place exclusively at C(6). Evidence is given that a chlorosulfonium intermediateCwas formed when the dichloroketothiosugar derivative6was treated with SO2Cl2. The carbene generated from the tosylhydrazone16rearranged to the enoses17–20, the migrating group coming in equal proportions from C(4) and C(6). Some stereochemical aspects of these reactions are discu

 

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