Heterolytic Fragmentation. A Class of Organic Reactions

Heterolytic fragmentation is a widespread but neglected class of organic reactions. It involves the regulated cleavage of molecules containing certain combinations of atoms such as carbon, oxygen, nitrogen, sulfur, phosphorus, silicon, boron and halogens. Fragmentation reactions are useful in degradation and structure elucidation, some are also of preparative value. A knowledge of the structural and electronic requirements makes it possible to predict and influence the course of reactions. From a theoretical viewpoint the recognition of heterolytic fragmentation has lead to the classification and correlation of a large number of apparently diverse reactions. Selected cases are reviewed in this article.