183508-69-2Relevant academic research and scientific papers
An unprecedented cleavage of the β-lactam ring: A novel synthesis of acyclic N,O- and N,S-acetals
Kita, Yasuyuki,Shibata, Norio,Kawano, Noriyuki,Yoshida, Naoki,Matsumoto, Keita,Takebe, Yasushi
, p. 2321 - 2329 (2007/10/03)
A new synthesis of acyclic N,O-acetals 3 and N,5-acetals 5 has been devised by way of a trimethylsilyl trifluoromethanesulfonate promoted formal 2,3-bond fragmentation of 4-heteroatom substituted azetidinones 1 and 4, respectively. This reaction proceeds by nucleophilic attack of a nitrite group of the solvent on the cation intermediate A. However, when there is a second nucleophile such as azidotrimethylsilane in the reaction system, no solvent attack occurs but, rather, the second nucleophile attacks the intermediate to form novel α-azido sulfides 6. Copyright 1996 by the Royal Society of Chemistry.
