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Condensed heterocycles Communication 43. Synthesis and transformations of benzo[b]selenopheno[3,2-d]-1,2,3-selenadiazoles and benzo[b]selenopheno[3,2-d]-l,2,3-thiadiazoles and a study of the molecular and crystal structure of dibenzo[b]selenopheno-[2,3-b;2,3-e]-1,4-diselenine

  • V. P. Litvinov
  • I. A. Dzhumaev
  • G. V. Gridunova
  • V. E. Shklover
  • Yu. T. Struchkov
  • B. M. Zolotarev
Organic Chemistry
  • 28 Downloads

Conclusions

  1. 1.

    Methods were developed for the synthesis of benzo[b]selenopheno[3,2-d]-1,2,3-thiadiazole and benzo[b]selenopheno[3,2-d]selenadiazole based on the reaction of the semicarbazone of 3-oxo-2,3-dihydrobenzo[b]selenophene with SOCl2 or SeO2, respectively.

     
  2. 2.

    The reaction of the selenadiazole with alcoholic alkali or the thermal decomposition of this compound gave dibenzo[2,3-b;2,3-e]-1,4-diselenine.

     
  3. 3.

    The major fragmentation processes of the M+. ions of the thiadiazoles and selenadiazoles upon electron impact is the consecutive loss of N2 and CS or CSe molecules, while in the case of the diselenine, the major process is the elimination of the heteroatoms.

     
  4. 4.

    A study was carried out on the crystal and molecular structure of dibenzo[b]selenopheno[2,3-g;2,3-e]-1,4-diselenine which revealed that this compound has trans configuration and twist boat conformation of the central heterocycle.

     

Keywords

Thermal Decomposition Electron Impact Fragmentation Process SeO2 Major Process 
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

© Plenum Publishing Corporation 1985

Authors and Affiliations

  • V. P. Litvinov
    • 1
    • 2
  • I. A. Dzhumaev
    • 1
    • 2
  • G. V. Gridunova
    • 1
    • 2
  • V. E. Shklover
    • 1
    • 2
  • Yu. T. Struchkov
    • 1
    • 2
  • B. M. Zolotarev
    • 1
    • 2
  1. 1.N. D. Zelinskii Institute of Organic ChemistryAcademy of Sciences of the USSRMoscow
  2. 2.A. N. Nesmeyanov Institute of Heteroorganic CompoundsAcademy of Sciences of the USSRMoscow

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