75909-63-6Relevant academic research and scientific papers
THE DEVELOPMENT OF AN ORGANOTRANSITION METAL SYNTHESIS OF QUINONES
Liebeskind, Lenny S.,Baysdon, Sherol L.,South, Michael S.,Iyer, Suresh,Leeds, James P.
, p. 5839 - 5853 (2007/10/02)
A new and very general synthesis of quinones is described from conception to the current state of maturity.The chemistry relies on a convergent joining of a transition metal complex and an alkyne to provide benzoquinones (from maleoylmetal complexes) and naphthoquinones (from phthaloylmatal complexes).Significant aspects of this chemistry are its generality (terminal, internal, electron rich, and electron deficient alkynes react), its mildness (reactions can be run between room temperature and 80 deg C) and its functional group compabtibility (aldehydes, ketones, esters, nitriles, olefins, halides acetals, ketals, etc. survive).
Reactions of Complex Ligands, XVII. Regiospecific Reaction of 1,4-Enynes with Pentacarbonyl(methoxyphenylcarbene)chromium(0): Preparation of Allyl-substituted 1-Naphthol- and 1,4-Naphthoquinone Derivatives
Doetz, Karl Heinz,Pruskil, Ingrid
, p. 2876 - 2883 (2007/10/02)
Pentacarbonyl(methoxyphenylcarbene)chromium(0) (1) and the enynes 2-5 react on warming in di-n-butyl ether to give the tricarbonyl(2(or 3)-alkyl-3(or 2)-allyl-4-methoxy-1-naphthol)chromium(0) complexes 6-9.Chromatography of these compounds on silica gel under atmospheric conditions results in decomplexation and formation of a naphthol- (9 -> 11) or a 1,4-naphthoquinone derivative (8 -> 10).Oxidation of 6-9 with silver(1) oxide leads exclusively to the quinones 12-14 and their tricarbonylchromium complexes 15-17.The products are characterized by spectroscopic methods.
