Nitration Studies. XI. Preparation of α-Nitroketones and Aldehydes. Nitration of Enol Acetates and Ethers<sup>1</sup>

Bachman, G. Bryant; Hokama, Takeo

doi:10.1021/jo01072a005

Cited by 17 publications

References 2 publications

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Formation of Carbon‐Hetero Atom Bonds by Free Radical Chain Additions to Carbon‐Carbon Multiple Bonds

Stacey

Harris

2011

Organic Reactions

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Free‐radical chain addition to carbon‐carbon multiple bonds to form carbon‐hetero atom bonds is an important synthetic method of wide scope. Carbon‐halogen, carbon‐sulfur, carbon‐silicon, carbon‐germanium, carbon‐phosphorus, and carbon‐nitrogen bonds have been formed by this method, In this chapter, the mechanism, scope, limitations, and experimental conditions are treated for the addition reactions that lead to the formation of the six types of carbon‐hetero atom bonds mentioned above. Since the direction of addition of free radicals to carbon‐carbon multiple bonds is common to all classes reviewed here, it is briefly explained.

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Formation of Carbon‐Hetero Atom Bonds by Free Radical Chain Additions to Carbon‐Carbon Multiple Bonds

Stacey

Harris

2011

Organic Reactions

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Electrophilic Amination of Carbanions, Enolates, and Their Surrogates

Ciganek

2009

Organic Reactions

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This chapter deals with the formation of carbon‐nitrogen bonds by reaction of carbon nucleophiles with electrophilic aminating reagents. The former encompass aliphatic and aromatic carbanions, enolates and their surrogates such as enamines, enol esters, and enol ethers, as well as carbanions stabilized by cyano or sulfone groups or by phosphorus. A section entitled Reagents and Mechanisms lists the many aminating reagents available and discusses the mechanisms by which the more important ones react. Among the electrophiles discussed are halo amines, various hydroxylamine derivatives, oxaziridines, imines, oximes, diazonium salts, diazo compounds, azo compounds, and azides. The section on Scope and Limitations is organized by carbon nucleophiles and attempts to suggest the best reagents for each class. A number of electrophilic aminating reagents that have been omitted from the scope of this chapter are briefly discussed, with references to reviews, in the section on Comparison with Other Methods. Tables listing references to the preparation of the various aminating reagents are found in the section on Experimental Conditions. References to the conversion of non‐amine products into amines are also provided there. The literature is covered to the middle of 2007.

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Nitryl chloride

Ho¹,

Fieser²,

Fieser³

2006

Fieser and Fieser's Reagents for Organic Synthesis

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Nitration Studies. XI. Preparation of α-Nitroketones and Aldehydes. Nitration of Enol Acetates and Ethers¹

Abstract: a-Xitroketones and aldehydes have been prepared in 12-3670 yields by the nitration of enol acetates and ethers with nitryl chloride. Other nitrating agents gave lower yields.

Cited by 17 publications

References 2 publications

Formation of Carbon‐Hetero Atom Bonds by Free Radical Chain Additions to Carbon‐Carbon Multiple Bonds

Formation of Carbon‐Hetero Atom Bonds by Free Radical Chain Additions to Carbon‐Carbon Multiple Bonds

Electrophilic Amination of Carbanions, Enolates, and Their Surrogates

Nitryl chloride

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Nitration Studies. XI. Preparation of α-Nitroketones and Aldehydes. Nitration of Enol Acetates and Ethers1

Abstract: a-Xitroketones and aldehydes have been prepared in 12-3670 yields by the nitration of enol acetates and ethers with nitryl chloride. Other nitrating agents gave lower yields.

Cited by 17 publications

References 2 publications

Formation of Carbon‐Hetero Atom Bonds by Free Radical Chain Additions to Carbon‐Carbon Multiple Bonds

Formation of Carbon‐Hetero Atom Bonds by Free Radical Chain Additions to Carbon‐Carbon Multiple Bonds

Electrophilic Amination of Carbanions, Enolates, and Their Surrogates

Nitryl chloride

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Product

Resources

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Nitration Studies. XI. Preparation of α-Nitroketones and Aldehydes. Nitration of Enol Acetates and Ethers¹