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Reaction of 1,3-diphenylnitrilimine with benzaldehyde phenylhydrazone

  • Organic Chemistry
  • Published:
Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    Benzaldehyde phenylhydrazone reacts with 1,3-diphenylimine, generated from 2,5-diphenyltetrazole (at 160°) or from benzoyl chloride phenylhydrazone (at either 80 or 25°), mainly with involvement of the NH group to give 1,4-diphenyl-2-benzylidenebenzhydrazidine, and only partially enters into 1,3-dipolar cycloaddition involving the C=N bond.

  2. 2.

    It was found that l,4-diphenyl-2-benzylidenebenzhydrazidine is thermally rearranged to benzil β-phenylosazone.

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Literature cited

  1. R. Huisgen, Angew. Chem.,75, 742 (1963).

    Google Scholar 

  2. R. Huisgen, J. Sauer, and M. Scidel, Chem. Ber.,94, 2503 (1961).

    Google Scholar 

  3. R. Huisgen and E. Aufderhaar, Chem. Ber.,98, 2185 (1965).

    Google Scholar 

  4. R. Huisgen, R. Grashey, and E. Aufderhaar, Chem. Ber.,98, 642 (1965).

    Google Scholar 

  5. B. I. Buzykin, L. P. Sysoeva, and Yu. P. Kitaev, Zh. Org. Khim.,10, 2200 (1974);11, 173, 348 (1975);12, 1557 (1976).

    Google Scholar 

  6. B. I. Buzykin, N. G. Gazetdinova, S. A. Flegontov, A. P. Stolyarov, and Yu. P. Kitaev, Zh. Org. Khim.,13, 1947 (1977).

    Google Scholar 

  7. B. I. Buzykin, G. D. Lezhnina, and Yu. P. Kitaev, Zh. Org. Khim.,11, 848, 1078 (1975).

    Google Scholar 

  8. M. Märky, H. Meler, A. Wunderli, H. Heimgarther, H. Schmid, and H.-J. Hansen, Helv. Chim. Acta,61, 1477 (1978).

    Google Scholar 

  9. H. M. Blatter and H. Lukaszewski, Tetrahedron Lett.,1968, 2701.

  10. R. Huisgen, K. Adelberger, E. Aufderhaar, H. Knupfer, and G. Wallbillich, Monatsh. Chem.,98, 1618 (1967).

    Google Scholar 

  11. G. E. Lewis and G. L. Spencer, Austral. J. Chem.,28, 1733 (1975).

    Google Scholar 

  12. I. Bhatnagar and M. V. George, J. Org. Chem.,32, 2252 (1967).

    Google Scholar 

  13. A. Gordon and R. Ford, Chemistry Manual [Russian translation], Mir (1976), p. 447.

  14. R. B. Woodward and C. Winter, Tetrahedron Lett.,1969, 2697.

  15. N. I. Christova and A. W. Spassov, Z. Chem.,18, 23 (1978).

    Google Scholar 

  16. H. Franzen, Ber.,42, 2467 (1909).

    Google Scholar 

  17. R. Engelhardt, J. Prakt. Chem.,54, 143 (1896).

    Google Scholar 

  18. M. Busch and R. Ruppenthal, Ber.,43, 3001 (1910).

    Google Scholar 

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Authors and Affiliations

  1. Kazan Branch of the Academy of Sciences of the USSR, A. E. Arbuzov Institute of Organic and Physical Chemistry, USSR

    B. I. Buzykin & N. G. Gazetdinova

Authors
  1. B. I. Buzykin
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  2. N. G. Gazetdinova
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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 7, pp. 1616–1620, July, 1980.

The authors express their gratitude to A. P. Stolyarov, Yu. Ya. Efremov, R. Z. Musing A. A. Vafina, and Z. S. Titova for recording the spectra.

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Buzykin, B.I., Gazetdinova, N.G. Reaction of 1,3-diphenylnitrilimine with benzaldehyde phenylhydrazone. Russ Chem Bull 29, 1159–1163 (1980). https://doi.org/10.1007/BF00949175

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  • DOI: https://doi.org/10.1007/BF00949175

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