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

Authors

  • C. C. Мочaлов M. V. Lomonosov Moscow State University, Moscow 119899
  • Д. B. Коcынкин M. V. Lomonosov Moscow State University, Moscow 119899
  • И. Д. Юдин M. V. Lomonosov Moscow State University, Moscow 119899
  • К. А. Заводских M. V. Lomonosov Moscow State University, Moscow 119899
  • Ю. С. Шабаров M. V. Lomonosov Moscow State University, Moscow 119899
  • Н. C. Зефиров M. V. Lomonosov Moscow State University, Moscow 119899

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.

How to Cite
Mochalov, S. S.; Kosynkin, D. V.; Yudin, I. D.; Zavodskikh, K. A.; Shabarov, Yu. S.; Zefirov, N. S. Chem. Heterocycl. Compd. 1994, 30, 413. [Khim. Geterotsikl. Soedin. 1994, 472.]

For this article in the English edition, see DOI https://doi.org/10.1007/BF01169933

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Published

1994-04-25

Issue

No. 4 (1994)

Section

Original Papers