Synthesis of enantiomerically pure (R,R)- and (S,S)-1,2-Bis(pentafluorophenyl)ethane-1,2-diamine and evaluation of the pK a value by ab initio calculations

Takashi Sakai, Toshinobu Korenaga, Noriyuki Washio, Yuji Nishio, Shinichi Minami, Tadashi Ema

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Abstract

1,2-Bis(pentafluorophenyl)ethane-1,2-diamine (1) was synthesized by the imino pinacol coupling of 4-methoxy-N-(pentafluorobenzylidene)benzylamine using a Zn-Cu couple and p-TsOH·H2O. The optical resolution of (±)-1 by means of chiral HPLC gave enantiomerically pure (R,R)- and (S,S)-1. The pKa value of 1 was estimated by a titration experiment and ab initio calculations, showing that 1 has a basicity comparable to aniline derivatives.

Original languageEnglish
Pages (from-to)1001-1008
Number of pages8
JournalBulletin of the Chemical Society of Japan
Volume77
Issue number5
DOIs
Publication statusPublished - May 1 2004

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ASJC Scopus subject areas

  • Chemistry(all)

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