Addition Reactions of Sulfenyl and Sulfinyl Chlorides with 3‐Phenyl‐1‐azabicyclo[1.1.0]butane

Abstract

The reactions of 3-phenyl-1-azabicyclo[1.1.0]butane with a-chlorosulfenyl chlorides and sulfinyl chlorides lead to the corresponding sulfenamides and sulfinamides, respectively, which possess an azetidine ring. It is proposed that a two-step mechanism occurs involving an intermediate carbenium ion, which is formed by the addition of the electrophile at the N-atom and cleavage of the N(1)ÀC(3) bond. The structures of 9b and 10b are established by X-ray crystallography.

Direct Alkylation of 1-Azabicyclo[1.1.0]butanes

“…It has been shown that 1-azabicyclo[1.1.0]­butanes can serve as powerful intermediates to prepare bis -functionalized azetidines in short order . Nagao and others have shown that ABB can be intercepted with various nucleophiles to prepare functionalized azetidines. , Recently, Baran has shown that ABB can be aminated with “turbo amides” in a one-pot fashion . The aforementioned studies inspired us to ponder whether ABB could be functionalized with carbon nucleophiles.…”