Thermolysis of 1,4-diazonaphthones in cyclic ethers

Abstract

1,4-Diazonaphthone, 3-methyl-1,4-diazonaphthone and 3-nitro-1,4- diazonaphthone were pyrolyzed in THF and dioxane to give different products. Spiro[naphthalene-1(4H), 2'-pyran]-4-one-3',4',5',6'- terhydro (5), 2-methyl-4-(2'- tetrahydrofuranyl)naphthol (6), 2-methyl- naphthol (7) and 1:1 polymer were produced in pyrol ysis of 3-methyl-1, 4- diazonaphthone in THF; Bis[(2-methyl-1,4-naphthylene)-22- crown-6] (8), spiro[1',4'-dioxepane-7',1(4H)-naphthalene-4- one] (9), 2-methyl- 4-(2'-dioxanyl)naphthol (10), 2-methyl- naphthol (7) and 1:1 polymer were produced in pyrolysis of 3-methyl-1,4-diazonaphthone in dioxane, Only 1:1 polymers were obtained in pyrolysis of 1,4-diazonaphthone in both THF and dioxane, 3-Nitro-1,4-diazonaphthone gave 2-nitro-4- (2'- tetrahydrofuranyl)naphthol (11), 2-nitro-naphthol (12) besides 1:1 polyme in THF. The reaction mechanism is discussed.

Key words: NAPHTHALENONE P, CYCLIC ETHER, DIAZO COMPOUNDS, THERMOLYSIS, KENONE P, DIAZOKETONE, REACTION MECHANISM

CLC Number:

O621.16

Cite this article

Zhang Wei;Mu Zonghong;Yang Li;Liu Zhongli. Thermolysis of 1,4-diazonaphthones in cyclic ethers[J]. Chin. J. Org. Chem., 2001, 21(2): 155-159.

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