Organic chemistry nucleophile

Carbon-carbon bond formation is fundamental to all of organic chemistry. Nucleophilic displacement is still the basis for most of what we do, but over the past thirty years radical addition and organometallic coupling have both been brought to a level of practical importance. 

Vinyl sulfones are useful building blocks for synthetic organic chemistry. Nucleophilic epoxida-tion of chiral (,S )-2-tosyl-2-cyclohexenol (1) and its 0-protected derivatives proceeds with excellent diastcrcosclcctivitics and good yields.. mt-Epoxides 2 of 98% optical purity are obtained, except for the silylated derivative which is much less selective when epoxidized with lithium tt-77-butylperoxide, and, similarly to the acetyl derivative, is incompatible with standard Weitz-Scheffer conditions68. 

The C-C and C-H bonds are also characteristically non-polar, as carbon and hydrogen have very similar electronegativities (the electronegativity difference is 0.4, C-H ). This means that alkane molecules are not susceptible to attack by the most common attacking agents in organic chemistry nucleophiles or electrophiles (electron pair donors or acceptors). 

Section 8 1 Nucleophilic substitution is an important reaction type m synthetic organic chemistry because it is one of the mam methods for functional group transformations Examples of synthetically useful nucleophilic sub stitutions were given m Table 8 1 It is a good idea to return to that table and review its entries now that the details of nucleophilic substitution have been covered... 

Carey Organic Chemistry I 17 Aldehydes and Ketones I Text Fifth Edition Nucleophilic Addition to... 

In the preceding chapter you learned that nucleophilic addition to the carbonyl group IS one of the fundamental reaction types of organic chemistry In addition to its own reactivity a carbonyl group can affect the chemical properties of aldehydes and ketones m other ways Aldehydes and ketones having at least one hydrogen on a carbon next to the carbonyl are m equilibrium with their enol isomers... 

Carey Organic Chemistry I 20 Carboxylic Acid Fifth Edition Derivatives Nucleophilic... 

You have already had considerable experience with carbanionic compounds and their applications in synthetic organic chemistry The first was acetyhde ion m Chapter 9 followed m Chapter 14 by organometallic compounds—Grignard reagents for example—that act as sources of negatively polarized carbon In Chapter 18 you learned that enolate ions—reactive intermediates generated from aldehydes and ketones—are nucleophilic and that this property can be used to advantage as a method for carbon-carbon bond formation... 

Addition Reactions. The addition of nucleophiles to quinones is often an acid-catalyzed, Michael-type reductive process (7,43,44). The addition of benzenethiol to 1,4-benzoquinone (2) was studied by A. Michael for a better understanding of valence in organic chemistry (45). The presence of the reduced product thiophenyUiydroquinone (52), the cross-oxidation product 2-thiophenyl-1,4-benzoquinone [18232-03-6] (53), and multiple-addition products such as 2,5-(bis(thiophenyl)-l,4-benzoquinone [17058-53-6] (54) and 2,6-bis(thiophenyl)-l,4-benzoquinone [121194-11-4] (55), is typical ofmany such transformations. 

The organic chemistry of thiocyanates is notably that of nucleophilic displacement of alkyl haHdes by thiocyanate anion to form alkyl thiocyanates ... 

One of the most important and general trends in organic chemistry is the increase in carbocation stability with additional alkyl substitution. This stability relationship is fundamental to imderstanding many aspects of reactivity, especially of nucleophilic... 

Carey Organic Chemistry, I 8. Nucleophilic Fifth Edition Substitution... 

When a Br nsted base functions catalytically by sharing an electron pair with a proton, it is acting as a general base catalyst, but when it shares the electron with an atom other than the proton it is (by definition) acting as a nucleophile. This other atom (electrophilic site) is usually carbon, but in organic chemistry it might also be, for example, phosphorus or silicon, whereas in inorganic chemistry it could be the central metal ion in a coordination complex. Here we consider nucleophilic reactions at unsaturated carbon, primarily at carbonyl carbon. Nucleophilic reactions of carboxylic acid derivatives have been well studied. These acyl transfer reactions can be represented by... 

Nucleophilic substitution of the halogen atom of halogenomethylisoxazoles proceeds readily this reaction does not differ essentially from that of benzyl halides. One should note the successful hydrolysis of 4-chloromethyl- and 4-(chlorobenzyl)-isoxazoles by freshly precipitated lead oxide, a reagent seldom used in organic chemistry. Other halides, ethers, and esters of the isoxazole series have been obtained from 3- and 4-halogenomethylisoxazoles, and 3-chloro-methylisoxazole has been reported in the Arbuzov rearrangement. Panizzi has used dichloromethylisoxazole derivatives to synthesize isoxazole-3- and isoxazole-5-aldehydes/ ... 

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