76941-51-0Relevant academic research and scientific papers
Stereoisomerization of Ketene Imines
Lambrecht, Johanna,Gambke, Brigitte,Seyerl, Joachim von,Huttner, Gottfried,Kollmannsberger-von Nell, Georg,et al.
, p. 3751 - 3771 (2007/10/02)
Barriers to racemization in solution of the ketene imines 1a - y and X-ray structures of the ketene imines 1s and z are described.Similar to allenes all ketene imines have dihedral angles of 90 deg between the C- and N-substituents.The barriers to racemization range from 30 to 63 kJmol-1 and are lowered by electron attracting substituents on C and N.The barriers of m- and p-substituted N-arylketene imines give a linear Hammett correlation with ?- constants.N-Arylketene imines racemize through inversion at nitrogen and simultaneous rotation of the aryl group around the N - aryl bond.
