Halogen Containing Compounds - Synthesis, Structure and Reactivity

Halogenations are the most common method for the functionalization of organic molecules, as halogen atoms (X) often serve as good handles for further chemical manipulations. In addition, halogenated compounds also play an important role in neighboring fields, such as pharmacy or medicine. Although electrophilic halogenation of Csp2 atoms constitutes the oldest and still most frequently used procedure to introduce X into a molecule, these strategies, however, often suffer from severe drawbacks, such as stereo- and regioselectivity issues as well as from environmental and/or safety concerns This lecture will provide mechanistic insights into the basic concepts of selective (chemo-, regio-, and stereoselective) halogenation reactions and will discuss the reactivitiy as well as the structure of halogenated organic compounds. The overall goal of the lecture is to understand the most important principles in organic halogen chemistry, in particular on a chemical mechanistic level. This includes: (A) the basic mechanisms involved in the formation of C,X bonds; (B) the problems associated with selective halogenations; (C) the biosynthesis of halogenated natural products; (D) the main principles in (catalytic) halogenation reactions.

At the end of the module students will be able to: (A) remember the importance/use of halogenated organic compounds and the problems associated with their preparation ; (B) Understand important general tactis in the context of the (bio)synthesis of halogenated compounds; (C) Apply the acquired knowlege in selective halogenation methodology to the preparation of unknown synthetic products; (D) Analyse and evaluate the mechanisms involved in the selective transformations and vice verse; (E) create on paper new catalysts/reagents which can in theory be applied for the selective introduction of halogen atoms.

Students are expected to have knowledge of basic organic chemistry.

The modules is designed as a lecture course that includes the presentation of the desired knowledge by power point slides and work on the blackboard. In addition, exercises will be jointly discussed and solved with the students throughout the lecture. Furthermore, the acquired knowledge will be trained by additional exercises asked to be solved as homework.

Tafelarbeit, PowerPoint, Übungsaufgeben

All material needed for the lecture will be provided during the course.

The final module examination consists of a written test, in which students are to remember what has been teached about the selective formation and the structure of carbon,halogen bonds without any tools, and where they are to apply this knowledge to new problem sets. Answering the questions requires own formulations as well as drawing and explaining chemical structures and reaction mechanisms.