
TY  - JOUR
A1  - Greenland, H 
A1  - Pinhey, JT 
A1  - Sternhell, S 
T1  - Oxidation of 1-Naphthols by Lead Tetraacetate in Acetic Acid
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1986
VL  - 39
IS  - 12
SP  - 2067
EP  - 2074
KW  - 
UR  - https://doi.org/10.1071/CH9862067 
N2  - 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 an 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. 
ER  -

