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• W2022238105 startingPage "4546" @default.
• W2022238105 abstract "Barriers to rotation of the N-alkenyl bond in a series of N-cycloalkenyl-N-benzyl acetamide derivatives have been measured in different solvents by variable-temperature NMR experiments. The barriers range from 9.7 to 14.2 kcal/mol, depending on substituents on the acetamide acyl group. Polar solvents such as chloroform and methanol increase the barrier to rotation compared to nonpolar solvents such as toluene. The barrier to rotation of “mimics” for acetamide-based radicals are estimated. The relative order of the values of krot for different acyl groups parallels their reported Taft Es paramaters. For successful chirality transfer in 5-endo trig radical cyclization, it is evident that rotations would need to be significantly slower than those reported here." @default.
• W2022238105 created "2016-06-24" @default.
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• W2022238105 date "2011-05-05" @default.
• W2022238105 modified "2023-09-26" @default.
• W2022238105 title "Bond Rotation Dynamics of Enamides: The Effect of the Acyl Group and Potential for Chirality Transfer during 5-Endo Trig Radical Cyclizations" @default.
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• W2022238105 doi "https://doi.org/10.1021/jo200343z" @default.
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