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  Highly selective metal-graphite-induced reductions of deoxy halo sugars

Fürstner, A., & Weidmann, H. (1989). Highly selective metal-graphite-induced reductions of deoxy halo sugars. The Journal of Organic Chemistry, 54(10), 2307-2311. doi:10.1021/jo00271a012.

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 Creators:
Fürstner, Alois1, Author              
Weidmann, Hans1, Author
Affiliations:
1Institute of Organic Chemistry, Technical University Graz, A-8010 Graz, Austria, ou_persistent22              

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 Abstract: To explore the applicability of highly active metal-graphite reducing agents to polyfunctional compounds a variety of suitably protected chloro-, bromodeoxy- and deoxyiodohexopyranosides and hexofuranoses were each treated with potassium-graphite laminate (C8K) and zinc/silver-graphite, respectively, invariably leading to the efficient formation of olefinic products. However, while C8K in all cases causes dehydrohalogenation, zinc/silver-graphite reductions proceeded by dealkoxyhalogenation, results quite opposite to the formation of glycals by each of the reagents. In contrast, magnesium on graphite readily dimerizes Me 6-deoxy-6-iodo-α-D-glucopyranoside by a Wurtz reaction.

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Language(s): eng - English
 Dates: 1989-05-01
 Publication Status: Published in print
 Pages: 5
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1021/jo00271a012
 Degree: -

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Title: The Journal of Organic Chemistry
  Abbreviation : J. Org. Chem.
Source Genre: Journal
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Publ. Info: Washington, D.C. : American Chemical Society
Pages: - Volume / Issue: 54 (10) Sequence Number: - Start / End Page: 2307 - 2311 Identifier: ISSN: 0022-3263
CoNE: https://pure.mpg.de/cone/journals/resource/954925416967_1