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Synthesis 1986; 1986(4): 249-284
DOI: 10.1055/s-1986-31584
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New Applications of Tetracyanoethylene in Organic Chemistry

Alexander J. Fatiadi*
  • *Center for Analytical Chemistry, National Bureau of Standards, Gaithersburg, Maryland 20899, U. S. A.
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Publication History

Publication Date:
27 September 2002 (online)

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Recent applications of tetracyanoethylene in organic chemistry are reviewed; this survey is mainly concerned with selected reactions of tetracyanoethylene which have use or potential use in organic synthesis. Among other topics, this survey includes new information on molecular complexes, ozonization of alkenes and acetylenes (the Criegee reaction) dehydrogenation and tricyanovinylation reactions, reactions of tetracyanoethylene oxide, reactions with ketones and diketones, synthesis of heterocycles, cationic polymerization reactions, and industrial, and analytical applications. Cycloaddition reactions and reactions of tetracyanoethylene with organometallics are not included in this survey. 1. Introduction 2. Scope of the Review 3. Methods of Preparation 4. Toxicity and Handling 5. Chemical Reactivity 6. Tetracyanoethylene Oxide (Tetracyanooxirane); Chemical Reactivity 7. The Ozonization of Alkenes in the Presence of Tetracyanoethylene (The Criegee Reaction) 8. Tetracyanoethylene as a Dehydrogenation Agent 9. Molecular Complexes between Aromatic and Heterocyclic Compounds and Tetracyanoethylene 10. Reaction of Ketones and Diketones with Tetracyanoethylene 11. Tricyanovinylation Reactions via Tetracyanoethylene 12. Synthesis of Heterocycles via Tetracyanoethylene 13. Cationic Polymerization in the Presence of Tetracyanoethylene 14. Industrial Applications of Polymeric Tetracyanoethylene Complexes 15. Analytical Application of Tetracyanoethylene 16. Addenda