1,4-Diazabicyclo[2.2.2]octane (DABCO) - an Efficient Reagent in the Synthesis of Alkyl Tosylates or Sulfenates

Abstract

All articles of this category The bicyclic tertiary amine 1,4-diazabicyclo[2.2.2]octane (DABCO) is a promising substitute not only for the widely used but hazardous and hygroscopic base pyridine in the syntheses of alkyl tosylates 3 but also for triethylamine in the preparation of alkyl sulfenates 4 from sterically hindered alcohols 2 . In several provided examples the substrates 2 were completely converted into the desired products, e.g. the respective tosylates 3 , which minimized subsequent separation processes. The current protocol points, in a number of cases, to nonchlorinated solvents as good alternatives to chloroform or dichloromethane and offers a workup procedure for a larger scale reaction which relies on the removal of the side products by filtration instead of the traditional extraction method using several aqueous washings. tosylation - sterically hindered alcohols - sulfenic acid O -ester - 1,4-diazabicyclo[2.2.2]octane - DABCO