73696-30-7Relevant academic research and scientific papers
ACETOLYSIS OF α'-SULPHONAMIDO α-CHLORO AND α-DIAZO KETONES. A CONVENIENT SYNTHESIS OF 3-AZETIDINONES
Pusino, Alba,Saba, Antonio,Desole, Giuseppe,Rosnati, Vittorio
, p. 33 - 36 (2007/10/02)
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.
