6141-93-1

Upstream product

• 60-29-7 diethyl ether 
• 86-57-7 1-Nitronaphthalene 
• 6921-40-0 1-azidonaphthalene 
• 101772-02-5 2-(1H-tetrazol-5-yl)quinoline 
• 235-21-2 [1,2,3]triazalo[3,5-α]quinolone 
• 28912-93-8 1-naphthyldiazonium tetrafluoroborate 

Downstream Products

• 4444-35-3 [2,2']binaphthyl-1,1'-diyldiamine 
• 481-91-4 4,4'-diamino-1,1'-binaphthyl 
• 239-64-5 13H-dibenzocarbazole 
• 134-32-7 1-amino-naphthalene 

Relevant academic research and scientific papers

Copper(I)-catalysed homo-coupling of aryldiazonium salts: synthesis of symmetrical biaryls

Copper(I) triflate acts as an efficient stoichiometric reagent for the homo-coupling of aryldiazonium salts bearing electron-withdrawing group(s), to yield symmetrical biaryls in acetonitrile under mild reaction conditions. Aryldiazonium salts bearing electron-donating groups undergo the reaction by using catalytic amounts of a copper complex prepared in situ from copper(II) triflate and 2,2′-bipyridine with metallic copper as an ultimate reductant.

Rearrangement of 2-Quinolyl- and 1-Isoquinolylcarbenes to Naphthylnitrenes

2-Quinolylcarbene 23 and 1-isoquinolylcarbene 33 are generated by flash vacuum thermolysis (FVT) of the corresponding triazolo[1,5-a]quinoline and triazolo[5,1-a]isoquinoline 19 and 29, as well as 2-(5-tetrazolyl)quinoline and 1-(5-tetrazolyl)isoquinoline 20 and 30, respectively. These carbenes rearrange to 1- and 2-naphthylnitrene 21 and 31, respectively, and the nitrenes are also generated by FVT of 1- and 2-naphthyl azides 18 and 28. The products of FVT of both the nitrene and carbene precursors are the 2- and 3-cyanoindenes 26 and 27 together with the nitrene dimers, viz. azonaphthalenes 25 and 35, and the H-abstraction products, aminonaphthalenes 24 and 34. All the azide, triazole, and tetrazole precursors yield 3-cyanoindene 26 as the principal ring contraction product under conditions of low FVT temperature (340-400 °C) and high pressure (1 Torr N2 as carrier gas for the purpose of collisional deactivation). This ring contraction reaction is strongly subject to chemical activation, which caused extensive isomerization of 3-cyanoindene to 2-cyanoindene under conditions of low pressure (10-3 Torr). 2-Cyanoindene is calculated to be ca. 1.7 kcal/mol below 3-cyanoindene in energy; accordingly, high-temperature FVT of these cyanoindenes always gives mixtures of the two compounds with the 2-cyano isomer dominating. Photolysis of trizolo[1,5-a]quinoline 19 and triazolo[5,1-a]isoquinoline 29 in Ar matrixes causes partial ring opening to the corresponding 2-diazomethylquinoline 19′ and 1-diazomethylisoquinoline 29′. The photolysis of the former gives rise to a small amount of the cyclic ketenimine 22, the intermediate connecting 2-quinolylcarbene and 1-naphthylnitrene.