3982-19-2

Upstream product

• 56271-34-2 N-(p-toluenesulfonyl)-d,l-alanyl chloride 
• 76543-26-5 N-(3-diazo-1-methyl-2-oxopropyl)-4-methylbenzenesulphonamide 
• 72746-71-5 N-(3-chloro-1-methyl-2-oxopropyl)-4-methylbenzenesulphonamide 

Relevant academic research and scientific papers

ACETOLYSIS OF α'-SULPHONAMIDO α-CHLORO AND α-DIAZO KETONES. A CONVENIENT SYNTHESIS OF 3-AZETIDINONES

Acetolysis of tertiary sulfonyl amides 1b,d leads to chlorine cinesubstitution exclusively, while in the case of the secondary amides 1a,c,e, only products of β-elimination are obtained.Acetolysis of the related diazo ketones 2b,d bearing a tertiary nitrogen atom, leads to normal substitution of the diazo group exclusively, whereas with the corresponding secondary amides 2a,c,e a concurrent cyclization to the 3-azetidinones 9, 12 and 15 is observed.By decomposition of the same diazoketones 2a,c,e in the presence of catalytic amounts of Cu(CF3COCHCOCF3)2, the above 3-azetidinones are obtained in excellent yields.