Organic Nitrating Reagents

Abstract

Nitro compounds are vital raw chemicals that are widely used in academic laboratories and industries for the preparation of various drugs, agrochemicals, and materials. Thus, nitrating reactions are of great importance for chemists and are even taught in schools as one of the fundamental transformations in organic synthesis. Since the discovery of the first nitrating reactions in the 19th century, progress in this field has been constant. Yet, for many years the classical electrophilic nitration approach using a mixture of strong mineral acids dominated the field. However, in recent decades, the attention of researchers has focused on new reactivity and new reagents that can provide access to nitro compounds in a practical and straightforward way under mild reaction conditions. Organic nitrating reagents have played a special role in this field since they have enhanced reactivity. They also allow nitration to be carried out in an ecofriendly and sustainable manner. This review examines the development and application of organic nitrating reagents.

1 Introduction

2 Organic Nitrating Reagents

2.1 Alkyl Nitrites

2.2 Nitroalkanes

2.3 Alkyl Nitrates

2.4 N-Nitroamides

2.5 N-Nitropyrazole

2.6 N-Nitropyridinium Salts

3 Organic Nitrating Reagents Generated In Situ

3.1 Acyl Nitrates

3.2 Trimethylsilyl Nitrate

3.3 Nitro Onium Salts

4 Organic Nitronium Salts

5 Organic Nitrates and Nitrites

5.1 Ammonium Nitrates

5.2 Heteroarylium Nitrates

5.3 Other Organic Nitrates

5.4 Organic Nitrites

6 Conclusion and Outlook

Key words

nitration - nitryl radicals - nitronium ion - nitric oxide - nitro compounds - nitrates - nitrites

Publication History

Received: 30 November 2021

Accepted after revision: 10 January 2022

Article published online:
13 April 2022

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