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Synthesis 1983; 1983(7): 517-536
DOI: 10.1055/s-1983-30409
review
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Alkylation of Ketones and Aldehydes via their Nitrogen Derivatives

James K. Whitesell* , Marilyn A. Whitesell
  • *Department of Chemistry, The University of Texas at Austin, Austin, Texas 78 712, U.S.A.
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Publication History

Publication Date:
17 May 2002 (online)

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In this review, methods for the alkylation of aldehydes and ketones via formation of nitrogen derivatives such as enamines, metallated imines (imine anions), metallated N, N-dialkylhydrazones (N,N-dialkylhydrazone anions), dimetallated oximes (oxime dianions), and metallated O-methyloximes (O-methyloxime anions) are described. Scope, limitations, and advantages or disadvantages of the methods over comparative reactions of enolates are also mentioned. 1. Introduction 2. Enamines 2.1. Structure 2.2. Formation 2.3. Reactions 3. Metallated Nitrogen Derivatives 3.1. Structure and Regiochemistry of Imine Anions and Related Species 3.2. Formation of Imine Anions 3.3. Reactions of Imine Anions 3.4. Reactions of N,N-Dialkylhydrazone Anions 3.5. Reactions of Oxime Dianions and O-Methyloxime Anions