de.mpg.escidoc.pubman.appbase.FacesBean
English
 
Help Guide Disclaimer Contact us Login
  Advanced SearchBrowse

Item

ITEM ACTIONSEXPORT

Released

Journal Article

Highly Selective Metal-Graphite-Induced Reductions of Deoxy Halo Sugars

MPS-Authors
There are no MPG-Authors available
Locator
There are no locators available
Fulltext (public)
There are no public fulltexts available
Supplementary Material (public)
There is no public supplementary material available
Citation

Fürstner, A., & Weidmann, H. (1989). Highly Selective Metal-Graphite-Induced Reductions of Deoxy Halo Sugars. Journal of Organic Chemistry, 54(10), 2307-2311. doi:10.1021/jo00271a012.


Cite as: http://hdl.handle.net/11858/00-001M-0000-0010-25D8-C
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.