Tetrahedron

Reaktionen polyvalenter jodverbindungen—III: Umwandlung von olefinen in α-azidocarbonylverbindungen mit hilfe von C6H5J (OAc) 2(CH3) 3SiN3

J Ehrenfreund, E Zbiral

Index: Ehrenfreund,J.; Zbiral,E. Tetrahedron, 1972 , vol. 28, p. 1697 - 1704

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Citation Number: 25

Abstract

Pb (OAc) 4(CH3) 3SiN3 reacts with simple nucleophilic olefins to form mostly diazides and azide-acetoxy compounds, 2 while with steroidal olefines α-azidosteroidketones3 are afforded. Contrary to this result the title reagent reacts not only with nucleophilic but also with electrophilic double-bounds yielding α-azido-carbonyl compounds. Not any azide-acetoxy compound is formed. Compound 14 indicates that activation by an arylgroup is not ...