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6-Cyclopropyl- and 6-(1-methylcyclopropyl) 1,4-benzodioxanes: synthesis and nitration. Rearrangement of nitro substituted 6-cyclopropyl-1, 4-benzodioxanes using concentrated sulfuric acid

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

6-Cyclopropyl- and 6-(1-methylcyclopropyl)-1,4-benzodioxanes have been synthesized as the first cyclopropyl 1,4-benzodioxanes. It was shown that nitration of these compounds occurs with retention of the three carbon ring. In contrast to simple ethers of cyclopropylphenols, nitration leads only to 7-nitro-6-cyclopropyl- and 7-nitro-6-(1-methylcyclopropyl)-1, 4-benzodioxanes,respectively. Nitration of 7-nitro-6-cyclopropyl-1,4-benzodioxane occurs regioselectively to give exclusively the 7 8-dinitro product. The structure of the nitration products was confirmed by their rearrangement to the corresponding nitrosopropionyl-1,4-benzodioxanes.

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Authors
  1. S. S. Mochalov
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  2. D. V. Kosynkin
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  3. I. D. Yudin
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  4. K. A. Zavodskikh
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  5. Yu. S. Shabarov
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  6. N. S. Zefirov
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Additional information

M. V. Lomonosov State University, Moscow 119899. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 472–479, April, 1994. Original article submitted February 2, 1994.

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Mochalov, S.S., Kosynkin, D.V., Yudin, I.D. et al. 6-Cyclopropyl- and 6-(1-methylcyclopropyl) 1,4-benzodioxanes: synthesis and nitration. Rearrangement of nitro substituted 6-cyclopropyl-1, 4-benzodioxanes using concentrated sulfuric acid. Chem Heterocycl Compd 30, 413–419 (1994). https://doi.org/10.1007/BF01169933

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  • DOI: https://doi.org/10.1007/BF01169933

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