Selective copper(II)-mediated oxidative coupling of a nucleophilic reagent to the para-methyl group of 2,4,6-trimethylphenol.
A copper(II) neocuproine system has been developed for the efficient and very selective 1,6-addition of a nucleophile to the para-methyl group of 2,4,6-trimethylphenol. Crystallographic and spectroscopic data point towards the involvement of a micro-methoxo-micro-phenoxo-bridged copper species which appears to generate a highly reactive quinone methide intermediate that can be attacked by a nucleophilic reagent.
Boldron
Christophe
C
Leiden Institute of Chemistry, Gorlaeus Laboratories, Leiden University, P.O. Box 9502, 2300, RA Leiden, The Netherlands.
Ozalp-Yaman
Seniz
S
Gamez
Patrick
P
Tooke
Duncan M
DM
Spek
Anthony L
AL
Reedijk
Jan
J
D003300:Copper / Q000737:chemistry*; D003408:Cresols / Q000737:chemistry*; D018360:Crystallography, X-Ray; D000432:Methanol / Q000737:chemistry; D008745:Methylation; D008958:Models, Molecular; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010636:Phenols / Q000737:chemistry; D012996:Solutions; D013057:Spectrum Analysis
D003408:Cresols; D010636:Phenols; D012996:Solutions; D003300:Copper; C505148:2,4,6-trimethylphenol; D000432:Methanol