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Reaction of p-menthadiene diepoxides with amines and sodium azide

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

Conclusions

  1. 1.

    p-Menthadiene diepoxides react with amines with opening of the 8,9-epoxide ring. Under mild conditions ethylamine and a mixture of p-menthadiene cis- and trans-diepoxides form a 3∶2 mixture of 8-hydroxy-9-(ethylamino)-1,2-epoxy-cis-p-menthane and 8-hydroxy-9-(ethylamino)-1, 2-epoxy-trans-p-menthane. Isopropylamine and diethylamine react with the trans-diepoxide only.

  2. 2.

    The reaction of p-menthadiene diepoxides with sodium azide involves opening of the 1,2-epoxide ring to form a 1∶1 mixture of trans-2-hydroxy-1-azido-8,9-epoxy-trans-menthane and trans-1-hydroxy-2-azido-8,9-epoxy-trans-p-menthane.

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Authors and Affiliations

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

    L. A. Mukhamedova, F. G. Nasybullina & M. I. Kudryavtseva

Authors
  1. L. A. Mukhamedova
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  2. F. G. Nasybullina
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  3. M. I. Kudryavtseva
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 9, pp. 2066–2070, September, 1977.

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Mukhamedova, L.A., Nasybullina, F.G. & Kudryavtseva, M.I. Reaction of p-menthadiene diepoxides with amines and sodium azide. Russ Chem Bull 26, 1911–1915 (1977). https://doi.org/10.1007/BF00924388

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  • DOI: https://doi.org/10.1007/BF00924388

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