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Research on Chemical Intermediates

, Volume 44, Issue 12, pp 7657–7664 | Cite as

[9, 9]-Sigmatropic shifts in acid-catalyzed benzidine-type rearrangements

  • Hee Jung Park
  • Dong Hun Jung
  • Koon Ha ParkEmail author
Article
  • 37 Downloads

Abstract

Each of the three new hydrazobenzenes consisting of a hydrazobenzene conjugated with a 5-membered heterocyclic ring (furan or thiophene) at its two para positions, prepared from corresponding azo precursors, was used in the acid-catalyzed benzidine rearrangements. Both rearrangement and disproportionation occurred and product structures were characterized by spectroscopic data such as NMR, MS, and with CHN analysis. We confirm the largest [9, 9]-sigmatropic benzidine-type rearrangement in each case as a prominent pathway accompanied by disproportionation.

Keywords

Benzidine-type rearrangement [9, 9]-sigmatropic shift Azobenzene Hydrazobenzene Nitrobiarene 

Notes

Acknowledgements

We greatly acknowledge support from Korea Basic Science Institute.

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© Springer Nature B.V. 2018

Authors and Affiliations

  1. 1.Western Seoul Center, Korea Basic Science InstituteSeoulKorea
  2. 2.ST PharmSiheung-siKorea
  3. 3.Department of ChemistryChungnam National UniversityDaejonKorea

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