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

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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.

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Acknowledgements

We greatly acknowledge support from Korea Basic Science Institute.

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Authors and Affiliations

  1. Western Seoul Center, Korea Basic Science Institute, Seoul, 03759, Korea

    Hee Jung Park

  2. ST Pharm, Siheung-si, Korea

    Dong Hun Jung

  3. Department of Chemistry, Chungnam National University, Daejon, 34134, Korea

    Koon Ha Park

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  1. Hee Jung Park
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  2. Dong Hun Jung
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  3. Koon Ha Park
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Correspondence to Koon Ha Park.

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Park, H.J., Jung, D.H. & Park, K.H. [9, 9]-Sigmatropic shifts in acid-catalyzed benzidine-type rearrangements. Res Chem Intermed 44, 7657–7664 (2018). https://doi.org/10.1007/s11164-018-3579-6

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