79644-47-6Relevant academic research and scientific papers
7b-Methyl-7bH-cyclopentindene, an Unsubstituted Tricyclic Aromatic Annulene
Gilchrist, Thomas L.,Tuddenham, David,McCague, Raymond,Moody, Christopher J.,Rees, Charles W.
, p. 657 - 658 (1981)
The aromatic tricyclic annulene (4) has been synthesised by bis-decarbonylation of the dialdehyde (3); on heating (4) rearranged into the 2aH-isomer (6).
A New Synthesis of the Tricyclic Annulene 7b-Methyl-7bH-cyclopentindene
Lidert, Zev,Rees, Charles W.
, p. 499 - 500 (1982)
In a new versatile synthesis of the tricyclic annulene, 7b-methyl-7bH-cyclopentindene, the third ring is formed by an intramolecular aldol condensation rather than a cycloaddition reaction.
Phenol-Keto Tautomerism in Tricyclic Annulenes; Preparation and Properties of 7b-Methyl-2a,7b-Dihydrocyclopentinden-2-(2H)-one
McCague, Raymond,Moody, Christoffer J.,Rees, Charles W.
, p. 622 - 624 (1982)
The 2-'phenol' in the tricyclic annulene series appears to exist entirely in the keto form (4); the 'phenolate' anion is readily formed, and can be methylated on oxygen, or on carbon to give isomer (9) exclusively.
Tricyclic Annulenes. Part 2. Synthesis of 7b-Methyl-7bH-cyclopentindene
McCague, Raymond,Moody, Christopher J.,Rees, Charles W.
, p. 165 - 174 (2007/10/02)
Four routes have been developed to the tricyclic annulene, 7b-methyl-7bH-cyclopentindene (1), starting from the diester (2a), the tricyclic nitrile (6), or the tricyclic ketone (9).The best overall procedure involves the ketones (9a) and (15).The
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.
Dimethyl 7b-Methyl-7bH-cyclopentindene-1,2-dicarboxylate. A New 10?-Electron Aromatic System
Gilchrist, Thomas L.,Rees, Charles W.,Tuddenham, David
, p. 83 - 86 (2007/10/02)
The title compound (8a) is formed by the acid-catalysed elimination of methanol from the cycloadduct (7) of 3-methoxy-3a-methyl-3aH-indene and dimethyl acetylenedicarboxylate.Its physical and chemical properties are consistent with a 10?-electron aromatic periphery which sustanis a diamagnetic ring current.It is photochemically and thermally stable, but rearranges slowly in boiling xylene to the isomer (11) by a methyl shift.With copper(II) nitrate and acetic anhydride, it gives a mixture of mononitro-substitution products.Preliminary experiments show that decarbonylation of the dialdehyde (8e) with tris(triphenylphosphine)rhodium(I) chloride provides a route to the unsubstituted tricyclic annulene (8f).
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.
