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Bond rotation dynamics of N-cycloalkenyl-N-benzyl alpha-haloacetamide derivatives
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Guthrie, David B., Damodaran, Krishnan, Curran, Dennis P., Wilson, Paul and Clark, Andrew J. (2009) Bond rotation dynamics of N-cycloalkenyl-N-benzyl alpha-haloacetamide derivatives. The Journal of Organic Chemistry, Vol.74 (No.11). pp. 4262-4266. doi:10.1021/jo900491w ISSN 0022-3263.
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Official URL: http://dx.doi.org/10.1021/jo900491w
Abstract
Barriers to rotation of the N-alkenyl bond in a series of N-cycloalkenyl-N-benzyl alpha-haloacetamide derivatives have been measured by variable-temperature NMR experiments. The barriers range from 10 to 18 kcal/mol, depending on ring size and on substituents on the cycloalkene and the amide. The observed trends aid in the design of substituent combinations that provide resolvable enantiomers or diastereomers at ambient temperature. The compounds undergo 4-exo and 5-endo radical cyclizations at rates that may be faster or slower than the estimated rate of N-alkenyl bond rotation in the derived radicals, depending on the substituents.
| Item Type: | Journal Article | ||||
|---|---|---|---|---|---|
| Subjects: | Q Science > QD Chemistry | ||||
| Divisions: | Faculty of Science, Engineering and Medicine > Science > Chemistry | ||||
| Library of Congress Subject Headings (LCSH): | Chemical bonds, Ring formation (Chemistry), Radicals (Chemistry), Amides | ||||
| Journal or Publication Title: | The Journal of Organic Chemistry | ||||
| Publisher: | American Chemical Society | ||||
| ISSN: | 0022-3263 | ||||
| Official Date: | 5 June 2009 | ||||
| Dates: |
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| Volume: | Vol.74 | ||||
| Number: | No.11 | ||||
| Number of Pages: | 5 | ||||
| Page Range: | pp. 4262-4266 | ||||
| DOI: | 10.1021/jo900491w | ||||
| Status: | Peer Reviewed | ||||
| Publication Status: | Published | ||||
| Access rights to Published version: | Restricted or Subscription Access | ||||
| Funder: | National Science Foundation (U.S.) (NSF), National Institutes of Health (U.S.) (NIH), European Regional Development Fund (ERDF), Advantage West Midlands (AWM) |
Data sourced from Thomson Reuters' Web of Knowledge
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