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Synthesis 1973; 1973(8): 469-483
DOI: 10.1055/s-1973-22235
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Azomethine Ylids, Azomethine Imines, and Iminophosphoranes in Organic Syntheses

C. G. STUCKWISCH*
  • *Department of Chemistry, University of Miami, Coral Gables, Florida 33124, U. S. A.
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Publication History

Publication Date:
12 September 2002 (online)

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Azomethine ylids and imines undergo 1,3-cycloaddition reactions to give rise to a variety of heterocyclic compounds. Photolysis of azomethine imines yields 1,2-diazepin derivatives. Iminophosphoranes serve as precursors to carbodiimides, substituted hydrazines, and heterocyclic compounds and have potential application in the synthesis of stable diazonium salts. 1. Preparation of Dipolar Intermediates 1.1. Azomethine Ylids 1.2. Azomethine Imines 1.3. Iminophosphoranes 2. 1,3-Cycloaddition Reactions 2.1. Synthesis of Pyrroles, Reduced Pyrroles, and Condensed Pyrroles 2.2. Synthesis of 1,3a-Diazapentalenes 2.3. Synthesis of Pyrazoles, Pyrazolines, Pyrazolidines, and Related Compounds 2.4. Cycloadditions Involving a Heteroelement in the Dipolarophile 3. Photolytic Reactions 4. Miscellaneous Syntheses

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