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New systems for classical nitrosohalogenation of alkenes 1. Reactions of alkenes with ethyl nitrite in the presence of phosphorus halides and thionyl chloride

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Abstract

Studies of nitrosation of norbornene and norbornadiene derivatives and dimethyl tricyclo[4.2.2.02,5]deca-3,7-diene-9,10-cis-endo-dicarboxylate demonstrated that nitrosation of alkenes with EtONO-PHal3, EtONO-POHal3 (Hal = Cl or Br), and EtONO-SOCl2 systems can afford nitroso halides in high yields without the formation of by-products (ketones and oximes). The reactions with 5-substituted norbornenes are nonregioselective. The trans dimer of endo-5-trifluoromethyl-cis-exo-2-chloro-3-nitrosobicyclo[2.2.1]heptane was studied by X-ray diffraction.

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Authors and Affiliations

  1. Department of Chemistry, M. V. Lomonosov Moscow State University, 1 Leninskie Gory, 119992, Moscow, Russian Federation

    O. B. Bondarenko, A. Yu. Gavrilova, V. N. Tikhanushkina & N. V. Zyk

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  1. O. B. Bondarenko
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  2. A. Yu. Gavrilova
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  3. V. N. Tikhanushkina
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  4. N. V. Zyk
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Dedicated to Academician N. S. Zefirov on the occasion of his 70th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 2070–2080, September, 2005.

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Bondarenko, O.B., Gavrilova, A.Y., Tikhanushkina, V.N. et al. New systems for classical nitrosohalogenation of alkenes 1. Reactions of alkenes with ethyl nitrite in the presence of phosphorus halides and thionyl chloride. Russ Chem Bull 54, 2133–2144 (2005). https://doi.org/10.1007/s11172-006-0088-3

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  • DOI: https://doi.org/10.1007/s11172-006-0088-3

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