King, FD; Caddick, S; (2012) The acid-mediated ring opening reactions of α-aryl-lactams. Org Biomol Chem , 10 (16) 3244 - 3252. 10.1039/c2ob00012a.
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4-Aryl-azetidin-2-ones (β-lactams) undergo ring opening with triflic acid to give cinnamamides which, in benzene, react further to give 3-aryl-3-phenyl-propionamides. Prolonged reaction times in benzene give 3,3-diphenyl-propionamide via an aryl/phenyl exchange. Lactams of ring size 7 and higher also ring open, but only 7- and 8-membered rings give pure diphenylalkylamides. AlCl(3) only ring opens the 4-aryl-azetidinones.
|Title:||The acid-mediated ring opening reactions of α-aryl-lactams.|
|UCL classification:||UCL > School of BEAMS > Faculty of Maths and Physical Sciences > Chemistry|
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