Tetrahedron letters

Synthesis of protected allylic amines from allylic phenyl selenides: Improved conditions for the chloramine T oxidation of allylic phenyl selenides

JE Fankhauser, RM Peevey, PB Hopkins

Index: Fankhauser, John E.; Peevey, Richard M.; Hopkins, Paul B. Tetrahedron Letters, 1984 , vol. 25, # 1 p. 15 - 18

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Citation Number: 17

Abstract

Abstract Anhydrous chloramine T in methanol is a highly effective reagent for the conversion of allylic phenyl selenides to the corresponding rearranged N-allylic-p-toluenesulfonamides. The reaction presumably proceeds via an allylic selenimide intermediate which undergoes [2, 3]-sigmatropic rearrangement.