Skip to content Skip to navigation
University of Warwick
  • Study
  • |
  • Research
  • |
  • Business
  • |
  • Alumni
  • |
  • News
  • |
  • About

University of Warwick
Publications service & WRAP

Highlight your research

  • WRAP
    • Home
    • Search WRAP
    • Browse by Warwick Author
    • Browse WRAP by Year
    • Browse WRAP by Subject
    • Browse WRAP by Department
    • Browse WRAP by Funder
    • Browse Theses by Department
  • Publications Service
    • Home
    • Search Publications Service
    • Browse by Warwick Author
    • Browse Publications service by Year
    • Browse Publications service by Subject
    • Browse Publications service by Department
    • Browse Publications service by Funder
  • Help & Advice
University of Warwick

The Library

  • Login
  • Admin

Bond rotation dynamics of N-cycloalkenyl-N-benzyl alpha-haloacetamide derivatives

Tools
- Tools
+ Tools

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

Research output not available from this repository, contact author.
Official URL: http://dx.doi.org/10.1021/jo900491w

Request Changes to record.

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:
DateEvent
5 June 2009Published
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

Request changes or add full text files to a record

Repository staff actions (login required)

View Item View Item
twitter

Email us: wrap@warwick.ac.uk
Contact Details
About Us