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(t)Li, (Me3Si)2NNa and Me3SiSMe. The synthesis of beta-chlorovinyl tributylstannyl sulfides 14. is also described. The synthetic potential of the new sulfur compounds is discussed
Phthalimidesulfenyl Chloride. Part 4. Addition to Acetylenes and Synthetic Utilization of their Adducts / G. Capozzi; L. Gori; S. Menichetti; C. Nativi. - In: JOURNAL OF THE CHEMICAL SOCIETY. PERKIN TRANSACTIONS. I. - ISSN 0300-922X. - STAMPA. - -:(1992), pp. 1923-1928. [10.1039/p19920001923]
Phthalimidesulfenyl Chloride. Part 4. Addition to Acetylenes and Synthetic Utilization of their Adducts
CAPOZZI, GIUSEPPE;MENICHETTI, STEFANO;NATIVI, CRISTINA
1992
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(t)Li, (Me3Si)2NNa and Me3SiSMe. The synthesis of beta-chlorovinyl tributylstannyl sulfides 14. is also described. The synthetic potential of the new sulfur compounds is discussed
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