79348-83-7Relevant academic research and scientific papers
Access to polysubstituted naphthalenes and anthracenes via a retro-Diels–Alder reaction
Akin, Esra Turan,Erdogan, Musa,Dastan, Arif,Saracoglu, Nurullah
, p. 5537 - 5546 (2017)
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.
On the Gold-Catalyzed Generation of Vinyl Cations from 1,5-Diynes
Wurm, Thomas,Bucher, Janina,Duckworth, Sarah B.,Rudolph, Matthias,Rominger, Frank,Hashmi, A. Stephen K.
supporting information, p. 3364 - 3368 (2017/03/17)
Conjugated 1,5-diynes bearing two aromatic units at the alkyne termini were converted in the presence of a gold catalyst. Under mild conditions, aryl-substituted dibenzopentalenes were generated. Calculations predict that aurated vinyl cations are key intermediates of the reaction. A bidirectional approach provided selective access to the angular annulated product in high yield, which was explained by calculations.
A STUDY of the 13C NMR SHIFTS in TWO TETRADEHYDROCYCLODECABIPHENYLENES and RELATED ARYL and BIPHENYLENYLACETYLENES.
Wilcox, Charles F.,Weber, Karl A.
, p. 4425 - 4436 (2007/10/02)
The 13C spectra of 5,6,9,10-tetradehydrocyclodeca-benzobiphenylene, 1, and 5,6,9,10-tetradehydrocyclodeca-naphthobiphenylene, 2, are reported as are those of a number of simpler acetylenic hydrocarbons used as spectral references.Most of the shifts can be assigned unambiguously.The acetylenic shift assignments were verified by ortho-proton, sp-carbon sp(3)> decoupling experiments.A simple additive shift correlation is found for the hydrocarbons containing unstrained acetylenic groups.However, significant discrepencies are found for the 13C shifts for the strained hydrocarbons 1, 2, 1,2-bis(phenylethynyl)-benzene, 12, and 2,3-bis(phenylethynyl)naphthalene, 13.The discrepencies are particularily large for carbons near the triple bonds and are attributed to a combination of strain, rehybridization, and other proximity effects related to the interaction between the ortho-substituted acetylenic carbons.
