Conference Paper

The Au(III) catalytic effect on the molecular mechanism of the [3+2] cycloaddition reaction between (Z)-C,N-diphenylnitrone and nitroethene: MEDT computational study

November 2024

Conference: XXV International Symposium „Advances in the Chemistry of Heteroorganic Compounds”
At: Łódź (Poland)

Authors:

Aneta Wróblewska

Department of Organic Chemistry Faculty of Chemistry University of Lodz

Mikołaj Sadowski

Cracow University of Technology

Radomir Jasiński

Cracow University of Technology

The regio-stereoselectivity and the molecular mechanism of the Au(III)-catalysed [3+2] cycloaddition reaction of (Z)-C,N-diphenylnitrone with nitroethene were explored in the light of the DFT calculations. We found, that the presence of the Au(III) molecular segments, in the reaction environment, dramatically has changed the cycloaddition mechanism. In particular, the observed, single step mechanism under the thermal conditions, is replaced to stepwise, zwitterionic mechanism on three from four theoretically possible paths. Its is interesting, that we identified the firstexample of the stepwise mechanism leading to the 5-nitroisoxazolidine molecular segment. Earlier, only [3+2] cycloadditions leading to the 4-nitroisoxazolidines were incidentally described as a stepwise processes.

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Last Updated: 27 Sep 2024