Abstract

The reactions of acenaphthenequinone and its derivatives with different nucleophiles, organic and inorganic reagents are reviewed. This survey also covers their oxidation and reduction reactions, in addition to many known reactions such as Friedel Crafts, Diels-Alder, bromination and thiolation.

Highlights

  • The broad spectrum of applications of acenaphthenequinone and its derivatives as biologically active compounds, dyes, etc has prompted us to review their chemistry and uses

  • The syntheses of acenaphthenequinone (1) and its derivatives, which are based mainly on the use of starting materials having the carbon skeleton of 1 and their reactivity towards nitrogen nucleophiles have been discussed in the first part of this series [1]

  • Ring cleavage of acenaphthenequinone (1) with an aqueous potassium hydroxide solution in dimethylsulphoxide at room temperature led to formation of 1, 8-naphthaldehydic acid (2) which exists in equilibrium with the corresponding cyclic structure [2,3,4]

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Summary

Introduction

The broad spectrum of applications of acenaphthenequinone and its derivatives as biologically active compounds, dyes, etc has prompted us to review their chemistry and uses. The syntheses of acenaphthenequinone (1) and its derivatives, which are based mainly on the use of starting materials having the carbon skeleton of 1 and their reactivity towards nitrogen nucleophiles have been discussed in the first part of this series [1]. In this part, the reactions of acenaphthenequinones are reviewed

Ring opening and enlargement
Reduction
Pt EtOH
Protonation
Reaction with active methylene compounds
Reaction with aldehydes and ketones
Reaction with Wittig reagents
Reaction with magnesium and lithium reagents
H Ar 136
Friedel Crafts reaction
2.10. Reaction with phenolic compounds
2.11. Halogenation reactions
2.13. Alkylation reactions
2.14. Ketal derivatives
2.15. Reaction with phosphites and phospholanes
Findings
2.18. Reaction with nitrogen nucleophiles
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