4.5 Article

Selective synthesis of 4-thiomethyl-1,3-dioxolan-2-ones under microwave irradiation using an environmentally benign KF/Al2O3/PEG-400 system

Journal

RESEARCH ON CHEMICAL INTERMEDIATES
Volume 42, Issue 6, Pages 5873-5885

Publisher

SPRINGER
DOI: 10.1007/s11164-015-2410-x

Keywords

Glycerol carbonate; Thiol; PEG-400; Microwave irradiation; KF/Al2O3

Funding

  1. CNPq
  2. FAPERGS
  3. CAPES
  4. FINEP

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We describe a simple and rapid method for selective synthesis of 4-thiomethyl-1,3-dioxolan-2-ones promoted by KF/Al2O3 using PEG-400 as solvent under microwave irradiation. The protocol employs 3-O-tosyl glycerol 1,2-carbonate 1 and a diverse array of thiols 2 to afford corresponding 4-thiomethyl-1,3-dioxolan-2-ones 3 in good yield and short reaction time compared with conventional heating methods. Moreover, selective synthesis of 1,3-bis-arylthiopropan-2-ol 4 by a stoichiometric and temperature-controlling reaction is presented.

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