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.
Keywords: boranes ; nitroalkanes ; oxime ethers ; radical reactions ; radical traps ; Efficient Conjugate Additions ; Radical Reactions ; Hydroboration ; Nitration ; Salts ; Catecholborane ; Nitroalkanes ; Derivatives ; Convenient ; Library
Record created on 2011-12-16, modified on 2016-08-09