Catalytic hypervalent iodine oxidation of p-dialkoxybenzenes to p-quinones using 4-iodophenoxyacetic acid and Oxone.
A catalytic hypervalent iodine oxidation of p-dialkoxybenzenes using 4-iodophenoxyacetic acid (1) and 2KHSO5 x KHSO4 x K2SO4 (Oxone) was developed. Reaction of p-dialkoxybenzenes (2) with a catalytic amount of 1 in the presence of Oxone as a co-oxidant in 2,2,2-trifluoroethanol-water (1 : 2) gave the corresponding p-quinones (3) in excellent yields without purification. This procedure was applied to synthesis of blattellaquinone (9), the sex pheromone of the German cockroach, Blattella germanica.
Yakura
Takayuki
T
Graduate School of Medicine and Pharmaceutical Sciences, University of Toyama, Toyama, USA. yakura@pha.u-toyama.ac.jp
Yamauchi
Yû
Y
Tian
Yuan
Y
Omoto
Masanori
M
D000818:Animals; D000840:Anisoles / Q000737:chemistry*; D002384:Catalysis; D003058:Cockroaches / Q000737:chemistry; D007202:Indicators and Reagents; D007455:Iodine / Q000737:chemistry*; D007462:Iodobenzenes / Q000737:chemistry*; D010084:Oxidation-Reduction; D011809:Quinones / Q000138:chemical synthesis / Q000737:chemistry*; D012724:Sex Attractants / Q000138:chemical synthesis; D013464:Sulfuric Acids / Q000737:chemistry*
C534660:4-iodophenoxyacetic acid; D000840:Anisoles; D007202:Indicators and Reagents; D007462:Iodobenzenes; D011809:Quinones; D012724:Sex Attractants; D013464:Sulfuric Acids; C496919:blattellaquinone; D007455:Iodine; C048813:potassium peroxymonosulfuric acid