期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 76, 期 11, 页码 4546-4551出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo200343z
关键词
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资金
- National Science Foundation
- Engineering and Physical Science Research Council
- Advantage West Midlands (AWM)
- European Regional Development Fund (EDRF)
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [0956921] Funding Source: National Science Foundation
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 k(rot) for different acyl groups parallels their reported Taft E-s 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.
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