Chapter 23. Reactions of Nitrosoarenes with SH Groups

  1. Saul Patai
  1. P. Eyer and
  2. D. Gallemann

Published Online: 4 APR 2003

DOI: 10.1002/047085720X.ch23

Amino, Nitroso, Nitro and Related Groups

Amino, Nitroso, Nitro and Related Groups

How to Cite

Eyer, P. and Gallemann, D. (1996) Reactions of Nitrosoarenes with SH Groups, in Amino, Nitroso, Nitro and Related Groups (ed S. Patai), John Wiley & Sons, Ltd, Chichester, UK. doi: 10.1002/047085720X.ch23

Editor Information

  1. The Hebrew University, Jerusalem, Israel

Author Information

  1. Walther-Straub-Institut für Pharmakologie und Toxikologie, Ludwig-Maximilians-Universität München, Nußbaumstr. 26, D-80336 München, Germany. Fax: (089)-51452-224

Publication History

  1. Published Online: 4 APR 2003
  2. Published Print: 15 SEP 1996

Book Series:

  1. PATAI'S Chemistry of Functional Groups

Book Series Editors:

  1. Zvi Rappoport

Series Editor Information

  1. The Hebrew University, Jerusalem, Israel

ISBN Information

Print ISBN: 9780471951711

Online ISBN: 9780470857205



This chapter contains sections titled:

  • Introduction and Historical Remarks

  • Reaction Products and Pathways

    • Overview

    • Formation of the Semimercaptal Intermediate

      • Structural Elucidation

      • Kinetic Aspects of Semimercaptal Formation

    • Formation of the N-hydroxyarylamine and Its Secondary Products

      • N-hydroxyarylamine

      • The Bifurcation at the Semimercaptal Stage

      • Secondary Products

    • The Sulfenamide Cation Descendants

      • The Sulfinamide

        • Identification

        • Formation Mechanism and Kinetics

      • Sulfenamide and Arylamine

        • Formation and Identification

        • Remarks on the Formation Mechanism

      • Thio Ether

      • N-sulfenylquinonimines and Resultant Products

        • Monocyclic Products

        • Bicyclic Products

        • N-sulfenylquinonimine Formation from Nitrosophenols and Nitrosoanilines

    • Formation of N-hydroxysulfonamide

    • Reaction Pathways Involving Radical Intermediates

  • Biological Significance

    • Introduction

    • Monocyclic Nitrosoaromatics

      • Nitrosobenzene Generated from Nitrobenzene and Aniline

      • Nitroso-procainamide from Procainamide

      • 3-nitrosobenzamide

      • Nitroso Derivatives of Chloramphenicol

      • Nitroso Derivatives of Chloroanilines

      • Nitroso Derivatives of Sulfonamide Drugs

      • Nitroso Derivatives of Dinitrobenzenes

      • 4-nitrosophenetol from 4-phenetidine

      • 4-nitroso-N,N-dimethylaniline

    • Polycyclic Nitrosoaromatics

      • 4-nitrosobiphenyl from 4-aminobiphenyl

      • 2-nitrosofluorene from 2-acetamidofluorene

    • Heterocyclic Nitrosoaromatics

      • Nitrosoimidazoles from Nitroimidazoles

      • Heterocyclic N-oxygenated Compounds Derived from Food Mutagens

  • References