Martin Sulfurane - A Versatile Reagent for Organic Synthesis

Introduction

Martin Sulfurane, a diphenylsulfur compound, has been a versatile reagent in organic synthesis since the 1970s.

Figure 1

The Sulfurane is reactive towards active hydrogen compounds and is one of the reagents of choice for a class of reactions including dehydration, amide cleavage, epoxide formation, sulfinimine synthesis, oxidation and coupling. [¹] The Martine Sulfurane has been prepared from hexafluoro­-2-phenyl-2-propanol using KOH, diphenylsulfide and bromine. [¹] The general mechanism of action involves the rapid exchange of one of the alkoxy ligands on the sulfurane, followed by ionisation giving an alkoxysulfonium ion, which, in turn, undergoes E1 or E2 elimination. [²] Since Martin Sulfurane is a mild and neutral reagent, these reactions are quite compatible with a wide range of functional groups like carbamate, carbonyl, ester, ether, etc. The reagent is applicable to the synthesis of many natural products.

References

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