Russian Journal of Organic Chemistry

, Volume 41, Issue 7, pp 1055–1063 | Cite as

Reaction of 5-Aryloxytetrazoles with Dimethyl Sulfoxide and DMSO-Acetic Anhydride. Structure and Quantum-Chemical Calculations of 1-Methylsulfanylmethyl-5-(4-nitrophenoxy)tetrazole

  • H. A. Dabbagh
  • N. Noroozi Pesyan
  • A. Bagheri
  • S. Takemo
  • H. Hayashi


Decomposition of methyl 5-(4-nitrophenoxy)tetrazole-2-carboxylate in dimethyl sulfoxide at room temperature yields a mixture of 1-methylsulfanylmethyl-5-(4-nitrophenoxy)tetrazole, 1- and 2-methyl-5-(4-nitrophenoxy)tetrazoles, and 5-(4-nitrophenoxy)tetrazole. Methyl 5-aryloxytetrazole-2-carboxylates containing electron-donor substituents in the aryloxy group do not give rise to the corresponding products under analogous conditions. The reactions of 5-aryloxytetrazoles [Ar = 4-O2NC6H4, C6H5, 2,6-(MeO)2C6H3] with dimethyl sulfoxide in the presence of acetic anhydride lead to mixtures of 1- and 2-methylsulfanylmethyl-5-aryloxytetrazoles whose yield and ratio depend on the substituent in the aryloxy group. The structure of 1-methylsulfanylmethyl-5-(4-nitrophenoxy)tetrazole was studied by X-ray analysis, two-dimensional NMR spectroscopy (HSQC, HMBC, NOESY), and quantum-chemical methods (ab initio, AM1, PM3). A highly selective procedure was developed for the synthesis of 5-(4-nitrophenoxy)tetrazole.


Methyl Acetic Dimethyl Anhydride Sulfoxide 
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Copyright information

© MAIK “Nauka/Interperiodica” 2005

Authors and Affiliations

  • H. A. Dabbagh
    • 1
  • N. Noroozi Pesyan
    • 1
  • A. Bagheri
    • 1
  • S. Takemo
    • 2
  • H. Hayashi
    • 3
  1. 1.College of ChemistryIsfahan University of TechnologyIsfahanIran
  2. 2.Department of ChemistryOsaka Prefecture UniversityOsakaJapan
  3. 3.Department of Natural Product Chemistry, School of Agriculture and Biological ScienceOsaka Prefecture UniversityOsakaJapan

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