79289-44-4

Basic information

• Product Name: (+/-)-erythro-1-(diphenylmethylene)-4-(1-methoxyethyl)-3-oxo-1,2-diazetidinium inner salt
• CAS NO: 79289-44-4
• Molecular Weight: 294.353
• Mol File: 79289-44-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (+/-)-erythro-1-(diphenylmethylene)-4-(1-methoxyethyl)-3-oxo-1,2-diazetidinium inner salt(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-erythro-1-(diphenylmethylene)-4-(1-methoxyethyl)-3-oxo-1,2-diazetidinium inner salt(79289-44-4)
• EPA Substance Registry System: (+/-)-erythro-1-(diphenylmethylene)-4-(1-methoxyethyl)-3-oxo-1,2-diazetidinium inner salt(79289-44-4)

Safety Data

• Hazardous Substances Data: 79289-44-4(Hazardous Substances Data)

Upstream product

• 67819-24-3 α-bromo-β-methoxybutyric acid chloride 
• 5350-57-2 benzophenone hydrazone 
• 79289-20-6 benzophenone (+/-)-threo-α-bromo-β-methoxybutyrylhydrazone 
• 67819-24-3 α-bromo-β-methoxybutyric acid chloride 
• 79289-20-6 benzophenone (+/-)-erythro-α-bromo-β-methoxybutyrylhydrazone 

Downstream Products

• 80-68-2 DL-threonine 
• 72-19-5 rac-allo-threonine 

Relevant articles and documents

Synthesis and properties of 3-oxo-1,2-diazetidinium ylides

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.