254759-19-8Relevant articles and documents
Efficient room temperature copper(I) mediated 5-endo radical cyclisations
Clark, Andrew J.,Dell, Colin P.,Ellard, John M.,Hunt, Nicola A.,McDonagh, John P.
, p. 8619 - 8623 (1999)
Reaction of bromo-enamides with catalytic Cu(Me6-trien)Br at room temperature furnishes regioisomeric mixtures of unsaturated pyrrolidinones in a highly efficient manner via an initial 5-endo radical cyclisation reaction followed by an oxidatio
Bond rotation dynamics of N-cycloalkenyl-N-benzyl α-haloacetamide derivatives
Guthrie, David B.,Damodaran, Krishnan,Curran, Dennis P.,Wilson, Paul,Clark, Andrew J.
supporting information; experimental part, p. 4262 - 4266 (2009/09/08)
(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.
