Properties and Reactions of Substituted 1,2‐Thiazetidine 1,1‐Dioxides: Functionalization and Reactions at C(4) of the β‐Sultam

The introduction of functional groups at the 4‐position of the β‐sultam ring was realized by the synthesis of mono‐ and disubstituted derivatives by reactions of N‐silylated β‐sultams with electrophiles in the presence of BuLi or LDA. As electrophiles, ketones, chlorosilanes, a β‐sultam, CO₂, chloroformiate, halogen, azodicarboxylate, phenyltriazoledione, tosyl azide, 1,3,5‐triazine, propyl nitrate, and phenyl isocyanate were used. Furthermore, a number of derivatives of these substitution products were synthesized. All products were characterized by standard spectroscopic methods, and conformations were studied, supported by calculation.