76274-21-0Relevant academic research and scientific papers
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.
The Photochemistry of 2-Acetoxynaphthalen-1(2H)-ones
Greenland, Harry,Pinhey, John P.,Sternhell, Sever
, p. 1789 - 1796 (2007/10/02)
The photochemistry of the 2-acetoxynaphthalen-1(2H)-ones (4), (13), (20), and (26) has been examined.In each case there was rapid formation of a mixture of products, which arose either by homolytic dissociation of the C-OAc bond of by rearrangement involving acetoxy group migration.Two types of rearrangement were observed.The first involved 1,2-acetoxy group with C(2)-C(4) bond formation to give the dihydrocyclopropindenones (7), (15), (22), and (28).This reaction, which is stereospecific, yields the endo-6-acetoxy isomer only, and it is thought to proceed by a concerted non-ionic pathway.The second rearrangement, which is believed to have an ionic mechanism, resulted in formation of 3-acetoxynaphthols from naphthalenones (4) and (26), and 4-acetoxynaphthols form naphthalenones (13) and (20), in which the 3-position is substituted.
