89901-15-5Relevant academic research and scientific papers
Tricyclic annulenes. Part 3. Reactions of 7b-Methyl-7bH-cyclopentindene
McCague, Raymond,Moody, Christopher J.,Rees, Charles W.
, p. 175 - 182 (2007/10/02)
The chemical reactions of the tricyclic 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 reaction with tetracyanoethylene, 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.
Electrophilic Substitution in a Tricyclic Annulene
McCague, Raymond,Moody, Christopher J.,Rees, Charles W.
, p. 497 - 499 (2007/10/02)
Electrophilic aromatic substitution reactions of the annulene (4) are reported, together with an improved method for its preparation.
