Naphthalene-1, 8-diylbis (diphenylmethylium) as an organic two-electron oxidant: Benzidine synthesis via oxidative self-coupling of N, N-dialkylanilines

T Saitoh, S Yoshida, J Ichikawa

Index: Saitoh, Terunobu; Yoshida, Suguru; Ichikawa, Junji Journal of Organic Chemistry, 2006 , vol. 71, # 17 p. 6414 - 6419

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Citation Number: 29

Abstract

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 CC 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 ...