Chapter 18: Overview of the Chemical Reactions of Singlet Oxygen

Practical aspects of setting up and running successful singlet-oxygen reactions with organic and organometallic substrates are discussed. Experimental factors that limit the lifetime of singlet oxygen and decrease its reaction efficiency, are examined. The advantages and disadvantages of photochemical and chemical generation of singlet oxygen and guidelines on proper choice of photochemical sensitizer and chemical source of this novel reactive intermediate are presented. Optimal reaction vessel design is discussed for small, medium, and large-scale reactions. The key factors that influence the regio- and stereochemistry of the ubiquitous singlet oxygen ene, 2 + 2, 4 + 2, and heteroatom centered reactions, which are the core processes observed with both heterocyclic and biological substrates, are scrutinized.