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<p>The action of sodium nitrite and sodium nitrate was used to perform N-nitrosation and N-nitration of 3,3-bis(trifluoromethyl)-containing 2-azabicyclo[2.2.2]hept-5-enes and 2-azabicyclo[2.2.1]heptanes. A series of new <i>C</i>-, <i>N</i>-nitroso- and <i>N</i>-nitrosubstituted 3,3-bis(trifluoromethyl) derivatives of 2-azabicyclo[2.2.1]hept-5-enes and heptanes with various combinations of substituents (bromine, chlorine, and fluorine) was synthesized, and their physicochemical properties were studied. The obtained <i>N</i>-nitrosubstituted 2-azabicyclo[2.2.1]hept-5-enes demonstrated pronounced inertness toward the electrophilic halogenation of the double bond. Their halogenation with the formation of 5,6-dihalogen-containing adducts was carried out under the radical conditions without Wagner—Meerwein rearrangement.</p>

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N-Nitrosation and N-nitration of 3,3-bis(trifluoromethyl)-containing 2-azabicyclo[2.2.1]hept-5-enes and heptanes

  • 期刊论文

  • 发表日期：

    2025年5月1日

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  • S. S. Khokhlov,
  • A. V. Kutkin

摘要

The action of sodium nitrite and sodium nitrate was used to perform N-nitrosation and N-nitration of 3,3-bis(trifluoromethyl)-containing 2-azabicyclo[2.2.2]hept-5-enes and 2-azabicyclo[2.2.1]heptanes. A series of new C-, N-nitroso- and N-nitrosubstituted 3,3-bis(trifluoromethyl) derivatives of 2-azabicyclo[2.2.1]hept-5-enes and heptanes with various combinations of substituents (bromine, chlorine, and fluorine) was synthesized, and their physicochemical properties were studied. The obtained N-nitrosubstituted 2-azabicyclo[2.2.1]hept-5-enes demonstrated pronounced inertness toward the electrophilic halogenation of the double bond. Their halogenation with the formation of 5,6-dihalogen-containing adducts was carried out under the radical conditions without Wagner—Meerwein rearrangement.