Synlett ( IF 1.7 ) Pub Date : 2009-02-24 , DOI: 10.1055/s-0028-1087807 Sreejith Pooppanal
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.
中文翻译:
Martin Suulfurane-一种用于有机合成的多功能试剂
自1970年代以来,二苯硫化合物Martin Suulfurane一直是有机合成中的多用途试剂。
图1
硫磺烷对活性氢化合物具有反应性,并且是一类反应的选择试剂之一,该反应包括脱水,酰胺裂解,环氧化物形成,亚磺胺合成,氧化和偶联。[ 1 ]马汀硫化物是由六氟-2-苯基-2-丙醇使用KOH,二苯硫醚和溴制备的。[ 1 ]总体作用机理涉及在硫烷上快速交换一种烷氧基配体,然后电离生成烷氧基ulf离子,然后进行E1或E2消除。[ ²]由于Martin Suulfurane是一种温和的中性试剂,因此这些反应与各种官能团(如氨基甲酸酯,羰基,酯,醚等)完全相容。该试剂适用于许多天然产物的合成。