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

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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:	Date Event 5 June 2009 Published
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)

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