159184-68-6Relevant academic research and scientific papers
Hypervalent iodine oxidation of phenol derivatives using a catalytic amount of 4-iodophenoxyacetic acid and Oxone as a co-oxidant
Yakura, Takayuki,Omoto, Masanori,Yamauchi,Tian, Yuan,Ozono, Ayaka
experimental part, p. 5833 - 5840 (2010/09/11)
Reaction of p-substituted phenols 2 with a catalytic amount of 4-iodophenoxyacetic acid (1) and Oxone as a co-oxidant in tetrahydrofuran (THF) or 1,4-dioxane-water gave the corresponding p-quinols 3 in excellent yields. Reaction of p-dialkoxyarenes 4 in 2,2,2-trifluoroethanol- water gave the corresponding p-quinones 5 in excellent yield without purification. These reactions provide efficient and practical methods for the preparation of p-quinols and p-quinones from p-substituted phenols and p-dialkoxyarenes, respectively. This quinone synthesis was applied to synthesis of blattellaquinone (13), the sex pheromone of the German cockroach Blattella germanica.
2,5-Dihydroxybenzyl and (1,4-dihydroxy-2-naphthyl)methyl, novel reductively armed photocages for the hydroxyl moiety
Kostikov, Alexey P.,Popik, Vladimir V.
, p. 9190 - 9194 (2008/03/14)
(Chemical Equation Presented) Irradiation of alcohols, phenols, and carboxylic acids "caged" with the 2,5-dihydroxybenzyl group or its naphthalene analogue results in the efficient release of the substrate. The initial byproduct of the photoreaction, 4-hydroxyquinone-2-methide, undergoes rapid tautomerization into methyl p-quinone. The UV spectrum of the latter is different from that of the caging chromophore, thus permitting selective irradiation of the starting material in the presence of photochemical products. These photoremovable protecting groups can be armed in situ by the reduction of photochemically inert p-quinone precursors.
