SYNTHESIS AND PROPERTIES OF AZOLES AND THEIR DERIVATIVES. 68. [2+3] CYCLOADDITION OF 2-NITRO-1-PROPENE TO (<i>Z</i>)-C,N-DIPHENYLNITRONE RELATIVE TO AM1 AND AM1/COSMO QUANTUM-CHEMICAL CALCULATIONS

Authors

  • M. Микульска Institute of Organic Chemistry and Technology, Krakow University of Technology
  • Р. Ясиньски Institute of Organic Chemistry and Technology, Krakow University of Technology
  • А. Бараньски Institute of Organic Chemistry and Technology, Krakow University of Technology

DOI:

https://doi.org/10.1007/2809

Keywords:

nitroalkenes, nitrones, [2 3] cycloaddition, semiempirical AM1 quantum-chemical method

Abstract

Semiempirical AM1 and AM1/COSMO calculations were used to examine possible pathways for the [2+3] cycloaddition of 2‑nitro‑1‑propene to (Z)‑C,N‑diphenylnitrone. These reactions proceed in the gas phase through a concerted mechanism. The effect of toluene or nitromethane as a dielectric medium results in the appearance of zwitterionic intermediates on pathways leading to 3,4-cis- and 3,4-trans-4‑methyl-4-nitro-2,3-diphenylisoxazolidines.

How to Cite
Mikulska, M.; Jasiński, R.; Barański, A. Chem. Heterocycl. Compd. 2010, 46, 232. [Khim. Geterotsikl. Soedin. 2010, 288.]

For this article in the English edition see DOI 10.1007/s10593-010-0496-z

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Published

2015-11-26

Issue

No. 2 (2010)

Section

Original Papers