70662-30-5Relevant articles and documents
A facile synthesis of naturally occurring binaphthoquinones: Efficient oxidative dimerization of 4-alkoxy-1-naphthols using silver(II) oxide-40% nitric acid
Tanoue, Yasuhiro,Sakata, Kazunori,Hashimoto, Mamoru,Morishita, Shin-Ich,Hamada, Moritsugu,Kai, Norihisa,Nagai, Takeshi
, p. 99 - 104 (2007/10/03)
Oxidation of 4-alkoxy-1-naphthols with AgO-40% HNO3 occurred along with a dimerization to give the corresponding bi-1,4-naphthoquinones. The oxidative dimerization required one hydroxyl group and took place at its ortho position. This reaction was applicable to syntheses of naturally occurring binaphthoquinones, bivitamin K3 and 3,3′-bijuglone.
Oxidation of 1-Naphthols by Lead Tetraacetate in Acetic Acid
Greenland, Harry,Pinhey, John T.,Sternhell, Sever
, p. 2067 - 2074 (2007/10/02)
A detailed study of the lead tetraacetate-acetic acid oxidation of 1-naphthol, 4-acetoxy-1-naphthol, 2-methyl-1-naphthol, 2,3-dimethyl-1-naphthol and 1,2,3,4-tetrahydro-9-anthrol (17) has been carried out.In the case of 1-naphthol the major product was 4-acetoxy-1-naphthol (4), with 2,2-diacetoxynaphthalen-1(2H)-one (2) being the only other product formed in significant yield.Attack at C4 was again the main reaction with 4-acetoxy-1-naphthol, which gave 1,4-naphthoquinone as the major product.Acetoxylation occurred predominantly at C2 with 2-methyl-1-naphthol and 2,3-dimethyl-1-naphthol to give the naphthalen-1(2H)-ones (11) and (12) respectively.In both cases minor amounts of 4-acetoxylated derivatives and quinones were also produced. 1,2,3,4-Tetrahydro-9-anthrol (17) gave an analogous set of products, the yields of which showed as unusual concentration dependence.In dilute solution 10-acetoxy-1,2,3,4-tetrahydro-9-anthrol (19) was produced in high yield, whereas with a high substrate concentration a good yield of 9a-acetoxy-1,2,3,4-tetrahydroanthracen-9(9aH)-one (18) was obtained.
