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- W4240496654 abstract "Four isomeric pathways for the [2 + 3] cycloaddition of (E)-β-nitrostyrenes (1a–c) with (Z)-C,N-diphenylnitrone (2) in gas phase and in a dielectric medium corresponding to the relative permittivity of toluene was evaluated in terms of AM1 and AM1/COSMO calculations in order to predict the reaction regio- and stereoselectivity. It was found that in the gas phase reaction takes place in a concerted manner independent of the nitrostyrene used as a dipolarophile and the [2 + 3] cycloadduct formed. The activation barriers obtained indicate that paths B and D (Scheme 1) are favored. The highest activation barrier occurs on the path C. In toluene solution this trend changes and the reaction paths can be ordered in the sequence B > A > D > C. An increase in the polarity of the reaction medium elevates the activation barriers and in some cases changes the reaction mechanism. An increase in the electron-withdrawing character of the substituent in the benzene ring of (E)-β-nitrostyrene speeds up the reaction both in the gas phase and in toluene solution but does not affect the reaction regio- and stereoselectivity. Copyright © 2000 John Wiley & Sons, Ltd." @default.
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- W4240496654 date "2000-09-01" @default.
- W4240496654 modified "2023-10-10" @default.
- W4240496654 title "Regio‐ and stereoselectivity of [2 + 3] cycloaddition of (E)‐β‐nitrostyrenes to (Z)‐C,N‐diphenylnitrone in the light of AM1 and AM1/COSMO calculations" @default.
- W4240496654 doi "https://doi.org/10.1002/1099-1395(200009)13:9<489::aid-poc267>3.3.co;2-z" @default.
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