Cycloalkylations of N‐(ω‐Halogenoalkyl)‐substituted Macrocyclic Imides

With ω‐halogenoalkyl isocyanates, 2‐oxocyclododecane‐l‐carbonitrile is transformed under ring enlargement to 1‐(ω‐halogenoalkyl)‐2,14‐dioxo‐1‐azacyclotetradecane‐3‐carbonitriles. In the presence of base, these products undergo O‐ or C‐alkylation leading to bicyclic compounds. The C‐alkylation product 7 undergoes solvolysis to form a sixteen‐membered ring compound.