Electrochemical Debromination of 1-Aryl-1,2-dibromo-2-nitropropanes in Dimethyl Sulfoxide

Bong-Rae Cho, Eun Jeong Cho, Seung Jae Lee, Won Seok Chae

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Abstract

Electrochemical debromination reactions oferythro-dl-l-aryl-l,2-dibromo-2-nitropropanes la-d at a platinum electrode have been investigated by cyclic voltammetry in 0.10 M LiClO4/DMSO. The reactions produced (E)-l-ary--2-nitropropenes 2a-d in high yields. The cyclic voltammograms were irreversible and the reduction current decreased as the number of cycles increased. The peak potential for the reductions wavss are in the range of —0.51 to —0.56 V (vs Ag/Ag+) and show no clear trend with different aryl substituent. The current density increased as the concentration of the substrate increased. The slopes of the plots of log(I/A) vs log[C] are close to unity, indicating unimolecular processes. For all reactions, the Tafel slopes are in the range of 115-125 mV. The logarithm of the ratio iX/in at -0.16 V did not correlate with the Hammett substituent constants. From these results, the mechanism of these reactions is assessed.

Original languageEnglish
Pages (from-to)2077-2081
Number of pages5
JournalJournal of Organic Chemistry
Volume60
Issue number7
DOIs
Publication statusPublished - 1995

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Dimethyl Sulfoxide
Platinum
Electrodes
Cyclic voltammetry
Current density
Substrates
2-nitropropane
lithium perchlorate

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Electrochemical Debromination of 1-Aryl-1,2-dibromo-2-nitropropanes in Dimethyl Sulfoxide. / Cho, Bong-Rae; Cho, Eun Jeong; Lee, Seung Jae; Chae, Won Seok.

In: Journal of Organic Chemistry, Vol. 60, No. 7, 1995, p. 2077-2081.

Research output: Contribution to journalArticle

Cho, Bong-Rae ; Cho, Eun Jeong ; Lee, Seung Jae ; Chae, Won Seok. / Electrochemical Debromination of 1-Aryl-1,2-dibromo-2-nitropropanes in Dimethyl Sulfoxide. In: Journal of Organic Chemistry. 1995 ; Vol. 60, No. 7. pp. 2077-2081.
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