Name Reactions of Functional Group Transformations

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It presents an up-to-date account of forty-seven major classes of functional group transformations and also serves to interconnect them. The book includes reviews from leading scientists in their specialty areas—all organized uniformly, making it easy to access information. Topics are organized into the following sections: Asymmetric synthesis Reduction Oxidation Olefination Amine synthesis Carboxylic acid derivatives synthesis Miscellaneous functional group manipulations Each section includes a description of: The functional group transformation Mechanisms Synthetic utilities and applications for the reaction References to the primary literature The historical perspective Variations and improvementon the reaction Experimental details With nineteen contributors from academia and industry, some of whom discovered the reactions they describe, Name Reactions for Functional Group Transformations is a state-of-the-art resource for organic and medicinal chemists conducting research in industries such as pharmaceuticals, fine chemicals, ag-biotech, and polymers, as well as for graduate students in organic chemistry.

Organic reaction - Wikipedia

It is an ideal companion to the first volume of this series, Name Reactions in Heterocyclic Chemistry. See All Customer Reviews. Shop Textbooks. Add to Wishlist. However, that changed in , when Russian chemist Moses Gomberg first synthesized the carbon radical triphenylmethyl. Nowadays, we know that organic free radicals have tremendous biological and synthetic significance.

Name Reactions of Functional Group Transformations

Key to the chemistry of organic radicals is their structure. The carbon atom, with its single unpaired electron, is desperate to bond with another atom to obtain its full complement of electrons. As a result, free radicals are extremely reactive and have been implicated in a wide range of biological processes including aging and cancer development. Indeed, our growing knowledge of organic free radicals has helped us to understand many natural phenomena, from DNA synthesis to sunburn.

Organic free radicals also play many vital roles in industry, as they are instrumental in producing various materials such as plastics and synthetic rubber.

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Our first named reaction featuring free radicals is the Hunsdiecker reaction , which describes the process by which silver salts of carboxylic acids react with a halogen to produce an alkyl halide with one fewer carbon atom. Originally, the silver salts used in this reaction were prepared by treating various carboxylic acids with silver oxide. Fortunately, a range of strategies have been developed to overcome this problem — for example, using acid chlorides as a more reactive functional group, or using thallium I carboxylates in place of silver.

Another derivation of the Hunsdiecker reaction, the Barton modification, has proved very synthetically useful as it is compatible with almost all functional groups. The same year that the Hunsdieckers were producing their alkyl halides, German chemist Hans Meerwein and colleagues conducted a series of experiments to study the reaction of diazo compounds with alpha, beta-unsaturated carbonyl compounds.


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Following their pioneering work, the arylation of substituted alkenes with aryldiazonium halides in the presence of a metal catalyst has come to be known as the Meerwein arylation. In the Meerwein arylation, the aryldiazonium halide reagents are usually prepared through the diazotization of the aromatic amines using sodium nitrite and aqueous hydrohalic acids. Once prepared, the halides are reacted immediately with the alkenes in an organic solvent such as acetone or acetonitrile.

Functional group

This versatile reaction has proved useful in several successful synthesis campaigns and was instrumental in preparing a series of peptide mimetic aldehyde inhibitors of calpain, compounds with a diverse range of therapeutic uses. Discovered over three decades after the Hunsdiecker and Meerwein reactions, the Keck radical allylation describes the coupling of an alkyl halide with allyltributyltin under radical conditions to insert an allyl group. Keck determined that the reaction was generally for primary, secondary and tertiary alkyl bromides, and identified azobisisobutyronitrile AIBN as the most efficient catalyst to initiate the process.

Corey , Professor Emeritus at Harvard University, is scientific editorial advisor for this book.


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Corey won the Nobel Prize in Chemistry in for his development of the theory and methodology of organic synthesis, and was awarded the Priestley Medal in Request permission to reuse content from this site. Appendix 4.

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Again and again, one comes across surprising reaction possibilities of well-known reagents, or some lesser known variants of common transformations. Undetected location. NO YES.

Name Reactions of Functional Group Transformations

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