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

David B. Guthrie, Krishnan Damodaran, Dennis P. Curran, Paul Wilson, Andrew J. Clark

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14 Citations (Scopus)


(Chemical Equation Presented) Barriers to rotation of the N-alkenyl bond in a series of N-cycloalkenyl-N-benzyl α-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.

Original languageEnglish
Pages (from-to)4262-4266
Number of pages5
JournalThe Journal of Organic Chemistry
Issue number11
Publication statusPublished - 5 Jun 2009
Externally publishedYes

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