220236-96-4Relevant articles and documents
Synthesis of 4,4-disubstituted β-lactams by regiospecific electrophile- and silver-induced ring expansion of 2,2-disubstituted 1-methoxycyclopropylamines
De Kimpe, Norbert,Tehrani, Kourosch Abbaspour,Fonck, Gwendolien
, p. 6500 - 6503 (1996)
2,2-Disubstituted 1-methoxycyclopropylamines underwent regiospecific ring expansion to 1,4,4-trisubstituted 2-azetidinones by N-chlorination with tert-butyl hypochlorite and subsequent rearrangement with silver tetrafluoroborate. Upon thermolysis, 4,4-disubstituted β-lactams suffer a characteristic ring opening to afford β,γ-unsaturated carboxylic amides. The reduction of 1,4,4-trisubstituted 2-azetidinones with lithium aluminum hydride afforded 1,2,2-trisubstituted azetidines.