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Part B: Reactions and Synthesis pp 1–56Cite as

Alkylation of Nucleophilic Carbon Intermediates

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Part of the book series: Advanced Organic Chemistry ((AOC,volume Pt. B))

Abstract

Carbon-carbon bond formation is the basis for the construction of the molecular framework of organic molecules by synthesis. One of the fundamental processes for carbon-carbon bond formation is a reaction between a nucleophilic carbon and an electrophilic one. The focus in this chapter is on enolate ions, imine anions, and enamines, which are the most useful kinds of carbon nucleophiles, and on their reactions with alkylating agents. Mechanistically, these are usually SN2 reactions in which the carbon nucleophile displaces a halide or other leaving group. Successful carbon-carbon bond formation requires that the SN2 alkylation be the dominant reaction. The crucial factors which must be considered include (1) the conditions for generation of the carbon nucleophile; (2) the effect of the reaction conditions on the structure and reactivity of the nucleophile; (3) the regio- and stereoselectivity of the alkylation reaction; and (4) the role of solvents, counterions, and other components of the reaction media that can influence the rate of competing reactions.

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Authors and Affiliations

  1. University of Virginia, Charlottesville, Virginia, USA

    Francis A. Carey & Richard J. Sundberg

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  1. Francis A. Carey
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  2. Richard J. Sundberg
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Carey, F.A., Sundberg, R.J. (2001). Alkylation of Nucleophilic Carbon Intermediates. In: Part B: Reactions and Synthesis. Advanced Organic Chemistry, vol Pt. B. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-662-39510-3_1

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  • DOI: https://doi.org/10.1007/978-3-662-39510-3_1

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-662-38652-1

  • Online ISBN: 978-3-662-39510-3

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