Spectroscopic and structural aspects of the reactions of 1,4-quinones with sulfur and nitrogen nucleophiles


Bayrak N. , Tuyun A. F. , Yildirim H., Onul N.

COMPTES RENDUS CHIMIE, vol.17, no.6, pp.563-569, 2014 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 17 Issue: 6
  • Publication Date: 2014
  • Doi Number: 10.1016/j.crci.2013.10.022
  • Title of Journal : COMPTES RENDUS CHIMIE
  • Page Numbers: pp.563-569

Abstract

A series of 1,4-benzoquinone derivatives from 2,5-dichloro-3,6-diethoxy-1,4-benzoquinone and 2,6-dichloro-3,5-diethoxy-1,4-benzoquinone were prepared by nucleophilic substitution reactions of sulfur and nitrogen nucleophiles. Spectral techniques (H-1 NMR, C-13 NMR, FT-IR, and LC-MS) were employed to structurally characterize the reaction products of alkoxy, chloro substituted-1,4-benzoquinones with thiols and amines in the presence of sodium carbonate in ethanol at room temperature. The orientations and the regioselectivity of the reactions of alkoxy, chloro substituted-1,4-benzoquinones with various thiol and amine nucleophiles are discussed. (C) 2013 Academie des sciences. Published by Elsevier Masson SAS. All rights reserved.