Trotterisation

Trotterisation is a chemical process used to generate reactive intermediates, particularly in the context of preparing complex molecules. It involves the controlled, stepwise addition of a highly reactive reagent, often a carbene, carbenoid, or other electrophilic species, to a substrate to facilitate the formation of a new chemical bond with improved precision and selectivity.

The term is notably associated with the use of the Simmons–Smith reaction, where diiodomethane and a zinc-copper couple are employed to cyclopropanate alkenes. In this context, Trotterisation refers to the slow addition of reagents under controlled conditions to avoid side reactions and achieve desired regio- or stereoselectivity. The process allows chemists to fine-tune reaction conditions, enabling the formation of complex cyclopropane derivatives and other strained ring systems.

Developed in the mid-20th century, Trotterisation has advanced synthetic organic chemistry by providing a method to generate carbene and carbenoid intermediates selectively. Its applications extend to pharmaceuticals, materials science, and natural product synthesis, where precise molecular construction is crucial.

The technique generally requires careful control of temperature, concentration, and addition rates to optimize product yield and purity. While it increases reaction complexity compared to direct addition methods, Trotterisation offers enhanced control over reactive intermediates, reducing unwanted side reactions and improving overall efficiency in synthetic pathways.

Overall, Trotterisation is a valuable strategy in modern synthetic chemistry for manipulating reactive intermediates with high selectivity and precision.