20020-02-4Relevant articles and documents
Howard,Gilbert
, p. 2685 (1962)
Perchlorotriphenylene: A Compound with Severe Molecular Twisting?
Campbell, M. C.,Humphries, R. E.,Munn, N. M.
, p. 641 - 644 (1992)
Perchlorotriphenylene has been reported several times in the literature.However, there is inconclusive evidence that this compound has actually been prepared.Severe molecular twisting to relieve steric interactions of "ortho" chlorines may preclude any stable existence.The compound is discussed in context with other severely twisted molecules, and methods are proposed for its synthesis.
Kricka,Vernon
, p. 942 (1971)
Access to polysubstituted naphthalenes and anthracenes via a retro-Diels–Alder reaction
Akin, Esra Turan,Erdogan, Musa,Dastan, Arif,Saracoglu, Nurullah
supporting information, p. 5537 - 5546 (2017/08/22)
Naphthalene and anthracene nuclei are present in several natural and synthetic compounds. Due to their unique physical and chemical properties, access to functionalized naphthalenes and anthracenes has attracted the attention of both synthetic and medicinal chemists over the decades. In this study, successive Diels–Alder/retro-Diels–Alder reactions of dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate with various bicyclic alkenes in one pot to yield naphthalene and anthracene derivatives are reported. Using anti- and syn-cyclotrimers derived from the cyclotrimerization of benzobarrelene as alkene partner enabled efficient synthesis of trinaphthylene.
De novo synthesis mechanism of polychlorinated dibenzofurans from polycyclic aromatic hydrocarbons and the characteristic isomers of polychlorinated naphthalenes
Iino,Imagawa,Takeuchi,Sadakata
, p. 1038 - 1043 (2007/10/03)
Polychlorinated dibenzofurans (PCDFs) and polychlorinated naphthalenes (PCNs) are known to be emitted from municipal waste incinerators (MWIs) with polychlorinated dibenzo-p-dioxins (PCDDs). Two formation paths for PCDD/Fs could mainly work, which are condensation of the precursors such as chlorophenols and 'de novo' formation from carbon. However the correlation between the chemical structure of carbon and the resulting PCDD/Fs still remains unknown. In this study, the PCDD/Fs formation from polycyclic aromatic hydrocarbons (PAHs) and CuCl was examined at 400 under 10% O2. Coronene among the PAHs characteristically gave 1,2,8,9-T4CDF and the derivatives. These isomers clearly indicate that chlorination causes the cleavage of the C-C bonds in a coronene molecule and also that oxygen is easily incorporated from its outside to form 1,2,8,9-T4CDF. The symmetrical preformed structures in the coronene molecule enabled to amplify the de novo formation of the isomer. PCNs are also formed directly from these PAHs. Since there have been few reports on the formation mechanism of PCNs, this study will be a first step to know the whole formation paths. We also define the de novo synthesis as the breakdown reaction of a carbon matrix, since the word has been used without the precise definition.
The synthesis and assay of radiolabelled benzene derivatives
Hales, Neil J.,Heaney, Harry,Hollinshead, John H.,Ley, Steven V.
, p. 7741 - 7754 (2007/10/02)
Several new syntheses of 1- and 4-[14C]anisole have been investigated and routes from [14C]cyanide and from 2-[14C]acetone are described which are better than those previously reported. The key step in one of the syntheses was catalytic dehydrogenation of 1-[14C]cyclohexanone to 1-[14C]phenol. Degradation of 5,6,7,8-tetrachloro-3,4-dihydro-1,4-etheno-[14C]naphthalen-2-(1H)-on e (10) prepared from [14C]anisole and tetrachlorobenzene has shown that the key step had proceeded without scrambling of the label.
