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

Jens Hartung; Siegfried Hünig; Rainer Kneuer; Michaela Schwarz; Hermann Wenner

doi:10.1055/s-1997-1372

Synthesis 1997; 1997(12): 1433-1438
DOI: 10.1055/s-1997-1372

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

Jens Hartung¹ , Siegfried Hünig² , Rainer Kneuer, Michaela Schwarz, Hermann Wenner

¹Institut für Organische Chemie der Universität Würzburg, Am Hubland, D-97074 Würzburg, Germany, Fax +49(931)8884606; E-mail: hartung@chemie.uni-wuerzburg.de
²Institut für Organische Chemie der Universität Würzburg, Am Hubland, D-97074 Würzburg, Germany, Fax +49(931)8884606

Abstract

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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

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