Ring transformation of 1,2-thiazetidine 1,1-dioxides with Lewis acids: Formation of trans-1,2,3-oxathiazolidine 2-oxides and cis-aziridines

Article abstract of DOI:10.1016/00404-0399(50)1051I-

Treatment of 1,2-thiazetidine 1,1-dioxides (β-sultams) bearing a poor migratory substituent at C-3 with Lewis acids such as EtAlCl₂ and AlCl₃ provided trans-1,2,3-oxathiazolidine 2-oxides and/or cis-aziridines via the C-S bond cleavage and recyclization. cis-Aziridines and/or ketones were provided from the reactions of 3-aryl-β-sultams with SnCl₄, depending on the migratory aptitude of the C-3 aryl substituent and configuration of C-3 and C-4 groups.