A facile synthesis of nitroalkenes from arylalkenes using I2/NO3 -" or KI/NO3 -

J. J. Kulmanakova, I. A. Perederina, M. S. Yusubov, Ki Whan Chi

Research output: Chapter in Book/Report/Conference proceedingConference contribution

Abstract

It has been established that in the reaction of arylalkenes with a combination of iodine and nitrates in glacial acetic acid, nitro alkenes are formed. The reaction conditions are simple, reagents are readily available and low-toxic. This is a basic advantage of our method by comparison with already known ones. The synthesis of nitroalkenes undergoes by the formation of intermediate vicinal iodonitroalkanes. In a number of experiments using a reaction of I2 and NO3 - with stylbene in acetic acid, 1-iodo2-nitro-1,2-diphenylethane was preoperatively derived. When the substrate was styrene, the product of addition β-nitrostyrene was formed. Beside of desired nitroalkenes and intermediate vicinal iodonitroalkanes, the reaction also provides compounds containing an acetate group in their structures. Using stylbene as a substrate, a dependent of a desired product nitrostylbene yield on varying different reagents quantity was studied. We have found that the presence of iodine is necessary in the reaction of desired product formation. We studied KI/NaNO3/AcOH system reactions with deactivated and activated unsaturated compounds. It has been found that unsaturated substrates (p-nitrostylbene, 4,4′-dinitrostylbene) form nitro derivatives, whereas cinnamic acid and its methyl ester are inert to KI/NaNO3 in acetic acid. When a substrate is activated (vinyl acetate), the main product is 2-iodoacetaldeyde.

Original languageEnglish
Title of host publication5th Korea-Russia International Symposium on Science and Technology - Proceedings: KORUS 2001
PublisherInstitute of Electrical and Electronics Engineers Inc.
Pages189-191
Number of pages3
Volume2
ISBN (Print)0780370082, 9780780370081
DOIs
Publication statusPublished - 2001
Event5th Korea-Russia International Symposium on Science and Technology, KORUS 2001 - Tomsk, Russian Federation
Duration: 26 Jun 20013 Jul 2001

Other

Other5th Korea-Russia International Symposium on Science and Technology, KORUS 2001
CountryRussian Federation
CityTomsk
Period26.6.013.7.01

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Keywords

  • Nitroalkenes

ASJC Scopus subject areas

  • Clinical Biochemistry
  • Computer Networks and Communications
  • Biotechnology
  • Civil and Structural Engineering
  • Mechanics of Materials
  • Electronic, Optical and Magnetic Materials
  • Materials Chemistry
  • Surfaces, Coatings and Films

Cite this

Kulmanakova, J. J., Perederina, I. A., Yusubov, M. S., & Chi, K. W. (2001). A facile synthesis of nitroalkenes from arylalkenes using I2/NO3 -" or KI/NO3 - In 5th Korea-Russia International Symposium on Science and Technology - Proceedings: KORUS 2001 (Vol. 2, pp. 189-191). [975223] Institute of Electrical and Electronics Engineers Inc.. https://doi.org/10.1109/KORUS.2001.975223