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Bond rotation dynamics of enamides : the effect of the acyl group and potential for chirality transfer during 5-endo trig radical cyclizations
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Clark, Andrew J., Curran, Dennis P., Geden, Joanna V., James, Natalie and Wilson, Paul (2011) Bond rotation dynamics of enamides : the effect of the acyl group and potential for chirality transfer during 5-endo trig radical cyclizations. The Journal of Organic Chemistry, Vol.76 (No.11). pp. 4546-4551. doi:10.1021/jo200343z ISSN 0022-3263.
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Official URL: http://dx.doi.org/10.1021/jo200343z
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.
Item Type: | Journal Article | ||||
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Subjects: | Q Science > QD Chemistry | ||||
Divisions: | Faculty of Science, Engineering and Medicine > Science > Chemistry | ||||
Library of Congress Subject Headings (LCSH): | Chemistry, Organic, Chemical bonds, Ring formation (Chemistry) | ||||
Journal or Publication Title: | The Journal of Organic Chemistry | ||||
Publisher: | American Chemical Society | ||||
ISSN: | 0022-3263 | ||||
Official Date: | April 2011 | ||||
Dates: |
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Volume: | Vol.76 | ||||
Number: | No.11 | ||||
Page Range: | pp. 4546-4551 | ||||
DOI: | 10.1021/jo200343z | ||||
Status: | Peer Reviewed | ||||
Publication Status: | Published | ||||
Access rights to Published version: | Restricted or Subscription Access | ||||
Funder: | National Science Foundation (U.S.) (NSF), Engineering and Physical Sciences Research Council (EPSRC) |
Data sourced from Thomson Reuters' Web of Knowledge
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