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Author:

Xiao, Huan-Lan (Xiao, Huan-Lan.) | Yang, Cheng-Wen (Yang, Cheng-Wen.) | Zhang, Ni-Tao (Zhang, Ni-Tao.) | Zeng, Cheng-Chu (Zeng, Cheng-Chu.) (Scholars:曾程初) | Hu, Li-Ming (Hu, Li-Ming.) (Scholars:胡利明) | Tian, Hong-Yu (Tian, Hong-Yu.) | Little, R. Daniel (Little, R. Daniel.)

Indexed by:

Scopus SCIE

Abstract:

The anodic oxidation of aminophenols and their amino-protected derivatives was investigated by using cyclic voltammetry and preparative electrolysis methods. The results showed that like the catechols the amino-protected aminophenol could also undergo Michael addition, and that the benzenesulfonate group was regioselectively introduced at the meta-position of the amino group. In contrast, the expected products were not formed from the oxidation of unprotected aminophenols. Finally, a reaction mechanism is proposed. (C) 2012 Elsevier Ltd. All rights reserved.

Keyword:

S-Nucleophiles Michael addition Aminophenol Electrochemical synthesis

Author Community:

  • [ 1 ] [Xiao, Huan-Lan]Beijing Univ Technol, Coll Life Sci & Bioengn, Beijing 100124, Peoples R China
  • [ 2 ] [Yang, Cheng-Wen]Beijing Univ Technol, Coll Life Sci & Bioengn, Beijing 100124, Peoples R China
  • [ 3 ] [Zhang, Ni-Tao]Beijing Univ Technol, Coll Life Sci & Bioengn, Beijing 100124, Peoples R China
  • [ 4 ] [Zeng, Cheng-Chu]Beijing Univ Technol, Coll Life Sci & Bioengn, Beijing 100124, Peoples R China
  • [ 5 ] [Hu, Li-Ming]Beijing Univ Technol, Coll Life Sci & Bioengn, Beijing 100124, Peoples R China
  • [ 6 ] [Tian, Hong-Yu]Beijing Technol & Business Univ, Sch Food Chem, Beijing 100048, Peoples R China
  • [ 7 ] [Little, R. Daniel]Univ Calif Santa Barbara, Dept Chem & Biochem, Santa Barbara, CA 93106 USA

Reprint Author's Address:

  • 曾程初

    [Zeng, Cheng-Chu]Beijing Univ Technol, Coll Life Sci & Bioengn, Beijing 100124, Peoples R China

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Source :

TETRAHEDRON

ISSN: 0040-4020

Year: 2013

Issue: 2

Volume: 69

Page: 658-663

2 . 1 0 0

JCR@2022

ESI Discipline: CHEMISTRY;

JCR Journal Grade:2

CAS Journal Grade:3

Cited Count:

WoS CC Cited Count: 20

SCOPUS Cited Count: 19

ESI Highly Cited Papers on the List: 0 Unfold All

WanFang Cited Count:

Chinese Cited Count:

30 Days PV: 12

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