Nucleophile to carbonyl compounds

TABLE 1.2. Equilibrium constants for addition of nucleophiles to carbonyl compounds. ... 

The most useful methods for the formation of C-C bonds are based on the addition of C-nucleophiles to carbonyl compounds. Among the many variations of this basic scheme phosphorus ylides, capable of olefinating aldehydes or ketones in a single step, have proven to be exceedingly valuable reagents in organic synthesis. 

Bismuth-Catalyzed Addition of Silyl Nucleophiles to Carbonyl Compounds and Imines... 

The hydrogen-bond complex 5 and ion pair 6 are activated form of the carbonyl compounds. The nucleophilic addihon of carbon nucleophile to carbonyl compounds and imines may be accelerated by acid catalysis. Nucleophilic attack to carbonyl compounds or imine took place either by way of 5 or 6 to furnish addihon product. If HX activates carbonyl compound by forming hydrogen-bond complex 5 and nucleophilic addition takes place to give an adduct, the reaction is a hydro-gen-bond catalyzed reaction (Scheme 2.5). In contrast, when ion pair 6 is formed and nucleophilic addihon occurs, the reachon is a Br0nsted-acid-catalyzed reachon. 

Alcohols are generally prepared on insoluble supports by reduction of carbonyl compounds or by addition of carbon nucleophiles to carbonyl compounds, although other strategies have also been used (Figure 7.1). 

Additions of Heteroatom Nucleophiles to Carbonyl Compounds and Subsequent Reactions—Condensations of Heteroatom Nucleophiles with Carbonyl Compounds... 

Addition of Heteroatom Nucleophiles to Carbonyl Compounds in Combination with Subsequent SN1 Reactions of the Primary Product Acetalizations... 

The addition of one equivalent of a heteroatom nucleophile to carbonyl compounds was described in Section 9.1. However, if two or more equivalents of the heteroatom nucleophile are present, in many cases the initial addition products (formula A in Figure 9.12) react... 

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