Issue 0, 1984

Tricyclic [10]annulenes. Part 3. Reactions of 7b-methyl-7bH-cyclopent[cd]indene

Abstract

The chemical reactions of the tricyclic [10]annulene (1) are described. The annulene is rapidly hydrogenated to give the fully saturated hydrocarbon (2). It undergoes a substitution reaction with electrophiles and has been nitrated, acetylated, formylated, and sulphonated. The preferential sites of attack of electrophiles are C-5 and C-1. Although the annulene (1) does not undergo cycloaddition reactions with tetra-cyanoethylene, dimethyl acetylenedicarboxylate, or benzyne, it does react with 4-phenyl-1,2,4-triazole-3,5-dione in refluxing 1,2-dimethoxyethane to give the 2:1 adduct (17) and with chlorosulphonyl isocyanate to give the ring-expanded indenoazepine (19). Hydrolysis of (19) gives the amide (20), which shows some antiaromatic character.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1984, 175-182

Tricyclic [10]annulenes. Part 3. Reactions of 7b-methyl-7bH-cyclopent[cd]indene

R. McCague, C. J. Moody and C. W. Rees, J. Chem. Soc., Perkin Trans. 1, 1984, 175 DOI: 10.1039/P19840000175

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