Synthesis of unusual oxime ethers by reaction of tetranitromethane with B-alkylcatecholboranes

Chemistry : a European Journal
Monique LüthyPhilippe Renaud

Abstract

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.

References

Oct 12, 2002·The Journal of Organic Chemistry·Christine CadotPhilippe Renaud
Jun 19, 2003·Angewandte Chemie·Arnaud-Pierre Schaffner, Philippe Renaud
Aug 5, 2006·Angewandte Chemie·Arnaud-Pierre SchaffnerPhilippe Renaud
Dec 1, 2006·Organic Letters·Eveline KumliPhilippe Renaud
Apr 8, 2009·Bioorganic & Medicinal Chemistry·Stephen D LindellJonathan Shannon

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