Abstract
This review, including 245 references, describes the application of Lawesson’s reagent [2,4-bis(p -methoxyphenyl)-1,3-dithiaphosphetane-2,4-disulfide] LR in organic and organometallic syntheses. Thionations of carbonyl-containing compounds as well as unexpected reactions are shown for different applications (e.g. cyclizations, rerrangements, syntheses of heterocyclic compounds etc.). Syntheses of novel organometallic compounds by LR are also discussed.
1 Introduction
2 Mechanism of the Thionation Reaction Using Lawesson’s Reagent
3 Reactions with Carbonyl-Containing Compounds
3.1 Ketones
3.2 Esters and Lactones
3.3 Amides and Lactams
3.4 Amino Acids, Peptides, Nucleosides, and Nucleotides
3.5 Macrocycles and Polymers
4 Cyclization Reactions to Thiophenes, Thiazoles and Other Compounds
5 Synthesis of Heteroatom-Containing Compounds
5.1 Sulfur-Containing Heterocyclic Compounds
5.2 Phosphorus- and Sulfur-Containing Heterocycles
5.3 Other Phosphorus- and Sulfur-Containing Compounds
6 Synthesis of Organometallic Compounds
6.1 Transition Metals
6.2 Main Group Metals
7 Usage of Lawesson’s Reagent for Special Syntheses
7.1 Glycosidations
7.2 Transformation of Alcohols to Thiols
7.3 Reduction of Sulfoxides
7.4 Catalyst for Aldol Reactions
7.5 Preparation of Other Compounds
8 Unexpected Reactions Following the Usage of Lawesson’s Reagent
9 References
Key words
Lawesson’s reagent - thionation - organothiophosphorus reagent - heterocycles - sulfur-compounds - organometallic compounds
