20958-76-3Relevant academic research and scientific papers
Synthesis of Cyclic Azomethine Imines from Aza β-Lactams. Conversion of 3-Oxo-1,2-diazetidinium Tosylates into 1-Substituted 3-Oxo-1,2-diazetidinium Inner Salts
Taylor, Edward C.,Clemens, Robert J.,Davies, Huw M. L.
, p. 4567 - 4571 (2007/10/02)
Dehydrohalogenation of (α-haloacyl)hydrazones of benzophenone gives 1-(diphenylmethylene)-3-oxo-1,2-diazetidinium inner salts (2,5,6), which are hydrolyzed with 1 molar equiv of p-toluenesulfonic acid monohydrate in CH2Cl2 to give 3-oxo-1,2-diazetidinium
Synthesis and properties of 3-oxo-1,2-diazetidinium ylides
Taylor, Edward C.,Haley, Neil F.,Clemens, Robert J.
, p. 7743 - 7752 (2007/12/18)
Treatment of α-chloroacylhydrazones of diaryl and certain aralkyl and dialkyl ketones with sodium hydride in anhydrous tetrahydrofuran gives 1-(disubstituted methylene)-3-oxo-1,2-diazetidinium inner salts (ylides). The reaction pathway involves formation of the hydrazone anion followed by intramolecular SN2 halide displacement (with complete inversion at the α carbon) by the sp2 imine nitrogen. These 1-(disubstituted methylene)-3-oxo-1,2-diazetidinium ylides are reduced by sodium borohydride to give 1-substituted 1,2-diazetidin-3-ones, undergo dipolar cycloaddition reactions to give fused aza-β-lactams, and can be hydrolyzed with p-toluenesulfonic acid monohydrate to the p-toluenesulfonic acid salt of 1,2-diazetidinone.
