Heteroatom ManipulationEdited by
- E. Winterfeldt, Universität Hannover, Germany
In this volume, those functional groups containing heteroatoms that have gained importance in organic synthesis are dealt with in detail. The introduction of these various groups and their relevant transformations are described and the various aspects of chemoselectivity, regioselectivity and stereoselectivity are discussed. After a compilation of the synthetically most useful substitution processes, there is a series of chapters on the various types of acylation reactions and in this context the different methods of acyl group activation are discussed. As functional group protection is of very general importance for organic synthesis, a corresponding chapter is included. This is followed by a section on the preparation of carbonyl derivatives and the most important transformations and rearrangements of functional group derivatives. At the end of the volume one finds chapters on all types of elimination reactions and related thermal reactions together with a survey on fragmentation processes in organic synthesis.
Published: January 1992
- Displacement by Substitution Processes. Synthesis of alcohols and ethers. Synthesis of glycosides. Synthesis of amines and ammonium salts. Synthesis of nitroso, nitro and related compounds. Synthesis of sulfides, sulfoxides and sulfones. Synthesis of phosphonium ylides. Synthesis of halides. Formation of pseudohalides, nitriles and related compounds. Ritter-type reactions. Acylation-Type Reactions. Synthesis of acid halides, anhydrides and related compounds. Synthesis of activated esters and related compounds. Synthesis of amides and related compounds. Synthesis of thioamides and thiolactams. Synthesis of thioesters and thiolactones. Selenoesters of all oxidation states. Synthesis of iminium salts, orthoesters and related compounds. Inorganic acid derivatives. Protecting Groups. Alcohols, amines and thiols, including multiple protecting groups. Functional Group Interconversion. Carbonyl group derivatization. Use of carbonyl derivatives for heterocyclic synthesis. Functional group transformations via carbonyl derivatives. Degradation reactions. Functional group transformation via allyl rearrangement. 2,3-sigmatropic rearrangements. Polonovski- and Pummerer-type reactions and the Nef reaction. Elimination Reactions. Eliminations to form alkenes, allenes and alkynes and related reactions. Reductive elimination, vicinal deoxygenation and vicinal desilylation. The Cope elimination, sulfoxide elimination and related thermal reactions. Fragmentation reactions. Author index. Subject index.