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An olefinic group at C-3 in azetidin-2-ones has been transformed into a formyl group by ozonolysis, and into a dimethoxymethyl group by ozonolysis and subsequent treatment with trimethoxymethane <2001J(P1)2566>. ð126Þ ð127Þ ð128Þ Azetidines, Azetines and Azetes: Monocyclic ð129Þ Isomerization of cis-azetidin-2-ones to trans-azetidin-2-ones has been observed either thermally (Equation 130) <2000JOC4453> or in the presence of a base as a catalyst (Equation 131) <2000JOC3459>. A formyl group in azetidin-2-ones undergoes Wittig-olefination <2000JOC3459>.
Removal of t-butyldimethylsilyl (TBDMS) is reported on treatment with TBAF (Equation 146) <1996TL6495>. Magnesium monoperoxyphthalate in methanol successfully cleaved the N–N bond of N-(1-pyrrolidinyl)azetidin-2-one 372 (Equation 147) <2000AGE2893> and of N-(N9-methyl-N9-p-tolyl)aminoazetidin-2-ones <2003T10195> to give the corresponding 1-unsubstituted azetidin-2-ones. ð141Þ ð142Þ 57 58 Azetidines, Azetines and Azetes: Monocyclic ð143Þ ð144Þ ð145Þ Scheme 54 ð146Þ ð147Þ Reductive O-debenzylation yielded N-hydroxyazetidin-2-one 373 (Scheme 55) <2000T5719>.
3 Experimental Structural Methods The infrared (IR) spectra of azetidin-2-ones show a strong absorption around 1745 cmÀ1. However, the carbonyl group in N-benzyl- or benzhydryl-substituted azetidin-2-ones absorb at around 1770–1780 cmÀ1 <2003S2483>. The most powerful tool for the determination of relative stereochemistry of azetidin-2-ones is 1H NMR spectroscopy. 5 Hz for transderivatives. The 13C NMR spectra of azetidin-2-ones show the typical carbonyl resonance at 166–170. However, values outside this range are possible if strong electron-withdrawing or electron-donating groups are present on the adjacent carbon atoms.