17873-57-3Relevant academic research and scientific papers
Gold-Catalyzed Annulation of 1,8-Dialkynylnaphthalenes: Synthesis and Photoelectric Properties of Indenophenalene-Based Derivatives
Fard, Sara Tavakkoli,Sekine, Kohei,Farshadfar, Kaveh,Rominger, Frank,Rudolph, Matthias,Ariafard, Alireza,Hashmi, A. Stephen K.
supporting information, p. 3552 - 3559 (2021/02/05)
A simple gold-catalyzed annulation of 1,8-dialkynylnaphthalenes utilizing a cationic gold catalyst was developed. Such a peri-position of two alkynyl substituents has not been studied in gold catalysis before. Dependent on the substrate, the reactions either follow a mechanism involving vinyl cation intermediates or involve a dual gold catalysis mechanism which in an initial 6-endo-dig-cyclization generates gold(I) vinylidene intermediates that are able to insert into C?H bonds. Indenophenalene derivatives were obtained in moderate to high yields. In addition, the bidirectional gold-catalyzed annulation of tetraynes provided even larger conjugated π-systems. The optoelectronic properties of the products were also investigated.
Tellurium-Mediated Halogen Transer from Polyhaloalkanes to Diyne Acceptors
Blum, Jochanan,Baidossi, Wael,Badriech, Yacoub,Hoffman, Roy E.,Schumann, Herbert
, p. 4738 - 4742 (2007/10/02)
Elemental tellurium catalyzes transfer of halogen from (CHCl2)2, from C2HCl5 and from (CHBr2)2, to the phenylated diynes 1-3, 17, 20, and 24, in which the alkyne moieties are in close proximity.The process is associated with cyclorearrangement reactions by which halogenated polycycles are formed.In boiling C2HCl5, derivatives of 1,2-bis(phenylethynyl)benzenes afford 5-halogenated indenoindenes, 1,8-bis(phenylethynyl)naphthalene gives a chlorinated benzofluoranthene derivative, and 2,2'-bis(phenylethynyl) forms 9-chloro-14-phenylbenzanthracene.Diynes 25 and 26 in which the ethynyl functions are further removed from each other fail to yield halogenated products.Diyne 25 undergoes oxidative cyclization by which 1,3-diphenyldibenzocycloheptafuran (29) is formed.Compound 26 is transformed to hydrocarbon 32, which involves a phenyl ring walk and elimination of H2Te.
