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A Camouflagednido-Carborane Anion: Facile Synthesis of Octa-B-methyl-1,2-dicarba-closo-dodecaborane(12) and Its Deboration Reaction
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1999
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Enantioselective SynthesisBioorganic ChemistryOrtho-carborane YieldsEngineeringHeterocyclicNatural SciencesFacile SynthesisDiversity-oriented SynthesisCamouflagednido-carborane AnionOrganic ChemistryExhaustive MethylationDeboration ReactionOrganometallic CatalysisChemistryHeterocycle ChemistryNatural Product Synthesis4,5,7,8,9,10,11,12-Octamethyl Derivative 1Biomolecular Engineering
Facile, efficient, and economical is the exhaustive methylation of ortho-carborane, its isomers and its derivatives under Friedel–Crafts conditions utilizing MeI and AlCl3. Regioselectively, ortho-carborane yields the 4,5,7,8,9,10,11,12-octamethyl derivative 1 which has been degraded by using KOEt under autogenous conditions. The resulting camouflaged nido anion can be protonated (2⋅H) and finally converted to the per-B-methylated C2B9 closo cluster 3.