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The synthesis of functional derivatives of the [1-CB9H10]-anion by Brellochs reaction
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2005 (English)In: Journal of Organo metallic Chemistry, no 690, 2790-2795 p.Article in journal (Refereed) Published
Abstract [en]

Reactions of decarborane with various aldehydes in alkaline media were studied. The reactions with HCOH and 2-MeOC6H4-CHO give the corresponding arachno-carboranes [6-R-arachno-CB9H13]-(R=H, C6H4-2-OMe), whereas the reactions with C6H5CHO, 4-BrC6H4CHO, 4-MeCONHC6H4CHO and 2-SC4H3CHO result in the nido-carboranes [6-R-nido-CB9H11]-(R=C6H5, C6H4-4Br, C6H4-4-NHCOMe, 2-SC4H3). Both the arachno- and nido-carboranes can be easily oxidized with elemental iodine in an alkaline aqueous solution giving the corresponding closo-derivatives [2-R-closo-2-CB9H9]-. These closo-2isomers, under heating in solution, undergo rearrangement to more thermodynamically favorable closo-1-isomers [1-R-closo-1-CB9H9]-. The structure of (Bu4N)[1-(4-BrC6H4)-1-CB9H9] was determined using single crystal X-ray diffraction.

Place, publisher, year, edition, pages
2005. no 690, 2790-2795 p.
Keyword [en]
1-carba-closo-decaborate, Derivatives, Synthesis, X-ray structure
National Category
Organic Chemistry
URN: urn:nbn:se:uu:diva-73834DOI: doi:10-1016-/j.jorganchem.2005.01.052OAI: oai:DiVA.org:uu-73834DiVA: diva2:101745
Available from: 2005-06-30 Created: 2005-06-30 Last updated: 2011-01-11

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Sjöberg, Stefan
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Department of ChemistryOrganic Chemistry II
Organic Chemistry

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