89862-68-0Relevant academic research and scientific papers
Simple and condensed β-lactams. Part 20. Reaction of some 1-(4-methoxyphenyl)azetidin-2-ones with cerium(IV) ammonium nitrate (CAN): Trapping of the quinone imine intermediate with chloride and iodide anions
Fetter,Giang,Czuppon,Lempert,Kajtar-Peredy,Czira
, p. 4185 - 4200 (2007/10/02)
1-(4-Methoxyphenyl)azetidin-2-ones 12 and 13, when treated with cerium(IV) ammonium nitrate (CAN), afford either their N-deprotected derivatives (19, 26) or the chlorinated compounds 22 and 27, respectively, as the main products, depending on whether sodi
Synthesis of 1-Aryl-4-carboxymethyl-2-azetidinones
Ongania, Karl-Hans,Pawlowski, Renata
, p. 95 - 100 (2007/10/02)
The photochemically induced rearrangement of the 4-diazoacetyl-2-azetidinones 2a-d in water/acetonitrile leads exclusively to the title compounds 3a-d provided that certain reaction conditions are fulfilled.This is in contrast to the thermal, silveroxide catalysed Wolff-rearrangement of 2a in alcohols which always gives a mixture of 4, 5 and 6.The mechanism of the 1,4-ringopening of 2a to 5 and 6 is discussed. - Keywords: 1-Aryl-4-carboxymethyl-2-azetidinones, 1-Aryl-4-diazoacetyl-2-azetidinones, Diazomethane, Pentendicarboxylicacidesterhalfanilides, Wolff-Rearrangement
