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Synthesis 1978; 1978(3): 165-204
DOI: 10.1055/s-1978-24703
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New Applications of Malononitrile in Organic Chemistry - Part I

Alexander J. FATIADI*
  • *Institute for Materials Research, National Bureau of Standards, Washington, D. C. 20234, U. S. A.
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Publication Date:
05 April 2002 (online)

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Recent applications of malononitrile in organic chemistry are reviewed; an overview of the chemistry of substituted malononitriles is also included. New trends, mechanisms and synthetic methods employing malononitriles are discussed. Among other topics, this survey includes new information on malononitrile dimers and trimers, new Knoevenagel and Michael condensation reactions, reactions with cyclic polyketones, quinones, sulfur and organometallic compounds, and the synthesis of new heterocycles, pesticides, charge-transfer complexes, and solvatochromic dyes. 1. Introduction 2. Scope of the Review 3. Methods of Preparation 4. Toxicity and Handling 5. Physical Properties 6. Spectral Properties 7. Chemical Reactivity 8. Analysis 9. Dimerization 10. Trimerization 11. The Knoevenagel and Related Reactions 12. Syntheses via the Michael Reaction 13. Reaction of Cyclic Polyketones with Malononitrile 14. Reaction of Quinones with Malononitrile 15. Quinodimethanes 16. Pyrans, Thiapyrans, and Pyrylium and Thiapyrylium Salts 17. Reactions of Tropones, Tropolones, and Tropylium Salts with Malononitrile 18. Reaction of Cyclooctatrienone with Malononitrile 19. Miscellaneous Applications 20. Industrial Applications 21. Addenda