4705-95-7Relevant academic research and scientific papers
187. Acid-Catalyzed Cleavage of 1,4-Dimethyl-1,4-dihydronaphthalene 1,4-Endoperoxide. Reactivity of the Resulting Hydroxyperoxy Carbocation with Nucleophiles
Jefford, Charles W.,Rossier, Jean-Claud,Kohmoto, Shigeo,Boukouvalas, John
, p. 1804 - 1814 (2007/10/02)
In the presence of acids, 1,4-dimethyl-1,4-dihydronaphthalene 1,4-endoperoxie readily reacts with nucleophiles to produce methyl- and ring-substituted naphthalenes in high yields.The regioselectivity observed depends on the nucleophile.The key intermediate is shown to be the corresponding hydroperoxy carbocation which could be intercepted in certain cases prior to aromatization.The hydroperoxide also undergoes Hock-type cleavage and dimerization giving 2,3-dihydro-1-benzoxepins, 4-methyl-1-naphthol, and 1,2,5,6-tetraoxocane as by-products.
Functionalization of the Methyl Group of 1,4-Dimethyl-1,4-dihydronaphthalene-1,4-endoperoxide
Jefford, Charles W.,Rossier, Jean-Claude,Kohmoto, Shigeo,Boukouvalas, John
, p. 1496 - 1497 (2007/10/02)
The acid-catalysed cleavage of 1,4-dimethyl-1,4-dihydronaphthalene-1,4-endoperoxide gives the 4-hydroxy, methoxy, trifluoroacetoxy, formyloxy, bromo, and chloro methyl derivatives of 1-methylnaphthalene in yields of 36, 38, 52, 76, 77, and 100percent respectively when water, methanol, trifluoroacetic, formic, hydrobromic, or hydrochloric acids are used as reagents.
