Phthalimidesulfenyl chloride. Part 4. Addition to acetylenes and synthetic utilization of their adducts

Abstract

Both the stereo- and regio-chemical reactivity of the phthalimidesulfenyl chloride 1 towards symmetrical and terminal acetylenes and the reactivity of the adducts 3 and 5 with various nucleophiles has been investigated. Nucleophilic substitution of the phthalimide residue was achieved with MeLi, PhLi, Bu^tLi, (Me₃Si)₂NNa and Me₃SiSMe. The synthesis of β-chlorovinyl tributylstannyl sulfides 14 is also described. The synthetic potential of the new sulfur compounds is discussed.