55039-56-0Relevant academic research and scientific papers
1,8-Bis(diphenylmethylium)naphthalenediyl dication as an organic oxidant: Synthesis of benzidines via self-coupling of N,N-Dialkylanilines
Saitoh, Terunobu,Yoshida, Suguru,Ichikawa, Junji
, p. 4563 - 4565 (2004)
(Chemical equation presented) 1,8-Bis(diphenylmethylium)naphthalenediyl dications promoted oxidative coupling of various N,N-dialkylanilines to afford the corresponding para-coupled bisanilines, benzidines, in good to excellent yield. The dications were readily prepared from a cyclic ether precursor, derived from 1,8-dibromonaphthalene, via deoxygenation with a silylating reagent in 1,1,1,3,3,3-hexafluoro-2-propanol under anhydrous conditions.
Naphthalene-1,8-diylbis(diphenylmethylium) as an organic two-electron oxidant: Benzidine synthesis via oxidative self-coupling of N,N-dialkylanilines
Saitoh, Terunobu,Yoshida, Suguru,Ichikawa, Junji
, p. 6414 - 6419 (2007/10/03)
Naphthalene-1,8-diylbis(diphenylmethylium) exhibits a unique electron-transfer reduction behavior due to the close proximity of the two triarylmethyl cations, which form a C-C bond while accepting two electrons, leading to 1,1,2,2-tetraphenylacenaphthene. The preparation of the dication was readily accomplished under anhydrous conditions starting from a cyclic bis(triarylmethyl) ether, derived from 1,8-dibromonaphthalene. The process proceeded via deoxygenation accompanying the formation of a disiloxane on treatment with a silylating agent (Me3SiClO4 or Me 3SiOTf) in 1,1,1,3,3,3-hexafluoropropan-2-ol. The dication was successfully employed for oxidative coupling of N,N-dialkylanilines at the paraposition to afford the corresponding benzidines in good to excellent yield.
