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Synthesis of Unusual Oxime Ethers by Reaction of Tetranitromethane with B ‐Alkylcatecholboranes
Author(s) -
Lüthy Monique,
Schenk Kurt,
Renaud Philippe
Publication year - 2010
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201000680
Subject(s) - tetranitromethane , chemistry , halogen , radical , oxime , nitro , medicinal chemistry , nucleophilic substitution , nucleophile , alkyl , organic chemistry , nitration , catalysis
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.