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

• Autorzy: Radomir Jasiński , Maria Mikulska , Andrzej Barański
• Języki publikacji: EN

Abstrakty

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 [...]

Słowa kluczowe

EN

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

• Czasopismo: Open Chemistry
• Rocznik: 2013
• Tom: 11
• Numer: 3
• Strony: 404-412

Daty

wydano

2013-03-01

online

2012-12-28

Twórcy

autor

Radomir Jasiński

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

autor

Maria Mikulska

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

autor

Andrzej Barański

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

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Identyfikatory

DOI

10.2478/s11532-012-0169-0