The reaction mechanism of the [2+3] cycloaddition between α-phenylnitroethene and (Z)-C,N-diphenylnitrone in the light of a B3LYP/6-31G(d) computational study

• Authors: Radomir Jasiński , Maria Mikulska , Andrzej Barański
• Languages of publication: EN

Abstracts

EN

Abstract The analysis of reactivity indices suggests the polar nature of the [2+3] cycloaddition of a-phenylnitroethene to (Z)-C,N-diphenylnitrone. Similar conclusions can be drawn from the investigation of the reaction pathways using the B3LYP/6-31g(d) algorithm. This shows that the cycloaddition mechanism depends on the polarity of the reaction medium. A one-step mechanism is followed in the gas phase and toluene in all the theoretically possible pathways. In more polar media (nitromethane, water), a zwitterionic, two-step rather than a one-step mechanism occurs in the pathway leading to 3,4-trans-2,3,5-triphenyl-4-nitroisoxazolidine. Graphical abstract [...]

Keywords

EN

[2+3] cycloaddition; Nitrone; Nitroalkene; Mechanism; DFT calculations

• Publisher: De Gruyter Open
• Journal: Open Chemistry
• Year: 2013
• Volume: 11
• Issue: 3
• Pages: 404-412

Dates

published

1 - 3 - 2013

online

28 - 12 - 2012

Contributors

author

Radomir Jasiński

• Institute of Organic Chemistry and Technology, Cracow University of Technology, 31155, Cracow, Poland

author

Maria Mikulska

• Institute of Organic Chemistry and Technology, Cracow University of Technology, 31155, Cracow, Poland

author

Andrzej Barański

• Institute of Organic Chemistry and Technology, Cracow University of Technology, 31155, Cracow, Poland

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Identifiers

DOI

10.2478/s11532-012-0169-0