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 - 2004

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ethylenediamine
Alkalinity
Titration
Derivatives
Experiments
aniline
benzylamine

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

In: Bulletin of the Chemical Society of Japan, Vol. 77, No. 5, 2004, p. 1001-1008.

Research output: Contribution to journalArticle

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AU - Korenaga, Toshinobu

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AU - Minami, Shinichi

AU - Ema, Tadashi

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