Synlett 2009(7): 1187-1188  
DOI: 10.1055/s-0028-1088111
SPOTLIGHT
© Georg Thieme Verlag Stuttgart ˙ New York

Singlet Oxygen

Jean-Alexandre Richard*
Laboratoire de Chimie Bioorganique - Université et INSA de Rouen, UMR CNRS 6014 and FR CNRS 3038, COBRA - IRCOF, Rue Lucien Tesnière, 76130 Mont-Saint-Aignan, France.
e-Mail: jarichard2000@yahoo.fr;
Further Information

Publication History

Publication Date:
02 April 2009 (online)

Introduction

Like molecular oxygen ( [³] O2), singlet oxygen ( [¹] O2) plays an important role in atmospheric and biological processes. It is also a powerful and inexpensive organic reagent whose chemistry has been initiated by Foote and co-workers in the 1960’s (Figure  [¹] ). [¹]

Figure 1 Triplet (³O2) and singlet (¹O2) oxygen

Singlet oxygen can be synthesized by several ways. The oldest and simplest method consists in a mixture of hydrogen peroxide and sodium hypochlorite to form singlet oxygen, water and sodium chloride (Scheme  [¹] ). [²]

Scheme 1 Synthetic ways for the formation of ¹O2

The currently most widely used method is the use of triplet oxygen in the presence of light and a sensitizer (e.g., rose bengal, methylene blue, tetraphenylporphyrin, vide infra).

Storable singlet oxygen sources can also been used. For example, [¹] O2 can be obtained thanks to a mixture of tri­phenyl phosphite and ozone (O3) (via the formation of an ozonide intermediate), [³] the use of calcium peroxide diperoxohydrate (CaO2˙2H2O2), [4] or the use of 9,10-diphenyl­anthracene peroxide [5] and its water soluble analogue 1,4-endoperoxide of 3-(4-methyl-1-naphthyl)propionic acid. [6]

The reactions involving singlet oxygen are usually oxidations or addition reactions that afford clean reactions which are consistent with the concept of atom economy. [7] In this spotlight a special emphasis has been made for illustrating different types of organic reactions in the context of the total synthesis of natural products.

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