Cyclization reactions of 4-(3′-butenyl)azetidin-2-one a route to the carbopenam ring system

Cyclization of 4-(3′-butenyl)azetidin-2-one, $\text{2}$ initiated by electrophilic reagents such as I₂, Hg(OAc)₂ results in the formation of bicyclic β-lactams having the carbopenam ring skeleton. Reaction of $\text{2}$ with Br₂ results in simple addition of Br₂ to the double bond, while PhSBr gives a mixture of cyclization and addition products.