Synthesis of unusual oxime ethers by reaction of tetranitromethane with B-alkylcatecholboranes.
The reaction of tetranitromethane with B-alkylcatecholboranes leads to the formation of unusual dinitrooxime ethers. A tentative mechanism is provided, which suggests the involvement of extremely fast addition of alkyl radicals to tetranitromethane. The substitution of one of the nitro groups in the oxime ethers by nucleophiles (such as secondary amines, halogens and styrene) and by radicals generated from B-alkylcatecholboranes is reported.
Lüthy
Monique
M
Department of Chemistry and Biochemistry, University of Bern, Freiestrasse 3, 3012 Bern, Switzerland.
Schenk
Kurt
K
Renaud
Philippe
P
D001880:Boranes / Q000138:chemical synthesis / Q000737:chemistry*; D002396:Catechols / Q000737:chemistry*; D004987:Ethers / Q000138:chemical synthesis*; D015394:Molecular Structure; D010091:Oximes / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013774:Tetranitromethane / Q000737:chemistry*
D001880:Boranes; D002396:Catechols; D004987:Ethers; D010091:Oximes; D013774:Tetranitromethane