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2005
Azetidine derivatives
R 0045
Reductive Dehalogenation of 4-Halogenomethyl Azetidin-2-one Derivatives. Synof (4-Oxo-azetidin-2-yl)acetonitriles. — A variety of substituted 4-halogeno07- 089 thesis
methyl-β-lactam derivatives [cf. (I), (IV), (VIII)] are synthesized and the stability of
their lactam rings under reductive conditions is examined. Both the substituents connected to the four-membered ring and to the halogenomethyl group as well as the applied reduction method are found to have considerable influence on the ratio of the
resulting dehalogenated lactam and ring-opened amide products. Reduction using
Bu3SnH provides best results with respect to the cyclic dehalogenated products. Therefore, this method defines the best route to (4-oxo-azetidin-2-yl)acetonitriles such as
compounds (VI) and (IX). — (BOROS, E.; BERTHA, F.; FETTER*, J.; VIDA, L.;
KAJTAR-PEREDY, M.; CZIRA, G.; J. Chem. Res. 2004, 8, 558-563; Dep. Org.
Chem. Technol., Budapest Univ. Technol. Econ., H-1521 Budapest, Hung.; Eng.) —
H. Toeppel
2005
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