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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
Article

Abstract

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.

Keywords

Methyl Acetic Dimethyl Anhydride Sulfoxide 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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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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