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

Guthrie, DB and Damodaran, K and Curran, DP and Wilson, P and Clark, AJ (2009) Bond rotation dynamics of N-cycloalkenyl-N-benzyl α-haloacetamide derivatives. Journal of Organic Chemistry, 74 (11). 4262 - 4266. ISSN 0022-3263

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(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. © 2009 American Chemical Society.


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Item Type: Article
Status: Published
CreatorsEmailPitt UsernameORCID
Guthrie, DB
Damodaran, K
Curran, DPcurran@pitt.eduCURRAN
Wilson, P
Clark, AJ
Date: 5 June 2009
Date Type: Publication
Journal or Publication Title: Journal of Organic Chemistry
Volume: 74
Number: 11
Page Range: 4262 - 4266
DOI or Unique Handle: 10.1021/jo900491w
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 0022-3263
MeSH Headings: Acetamides--chemistry; Alkenes--chemistry; Cyclization; Kinetics; Molecular Conformation; Thermodynamics
PubMed ID: 19413296
Date Deposited: 21 Feb 2013 22:52
Last Modified: 02 Feb 2019 15:59


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