Reactions of Imidoselenium Compounds

Abstract

In 1976 Sharpless reported [592] that ß-pinene afforded the corresponding allylic amine when reacted in methylene chloride whith selenium diimides 63 and 64 (Schemes 250, 251) obtained from selenium tetrachloride and t-butyl amine (2 equiv.) or p-toluene sulfonamide (2 equiv.) respectively in the presence of an amine base (4 equiv.). Even better results have been observed [592] using reagent 65 (0.63 to 0.83 mol. equiv. around 20 °C. Scheme 250), although 64 and 65 should be structurally identical. Under these conditions side reactions leading to multiple allylic amination or to the corresponding diene are minimized [592].