A DFT study on the (2 + 3) cycloaddition reactions of 2‐nitropropene‐1 with Z‐C,N‐diarylnitrones |
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| Authors: | Radomir Jasiński Katarzyna W?sik Maria Mikulska Andrzej Barański |
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| Institution: | Institute of Organic Chemistry and Technology, Cracow University of Technology, 31‐155 Cracow, Poland |
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| Abstract: | B3LYP/6‐31G* calculations for competing (2 + 3)‐cycloaddition pathways for 2‐nitropropene‐1 (1) to Z‐C, N‐diarylnitrones ( 2a – e ) suggest a concerted reaction mechanism. However, the results point to the strongly asymmetric nature of transition complexes. Increasing polarity of the reaction environment and presence of electron‐donating substituents in the nitrone phenyl rings contribute to the higher asymmetry of these structures. Copyright © 2009 John Wiley & Sons, Ltd. |
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| Keywords: | DFT (2 + 3) cycloaddition nitrones nitroalkenes mechanism |
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