Synthesis of protected allylic amines from allylic phenyl selenides: Improved conditions for the chloramine T oxidation of allylic phenyl selenides
✍ Scribed by John E. Fankhauser; Richard M. Peevey; Paul B. Hopkins
- Book ID
- 104242326
- Publisher
- Elsevier Science
- Year
- 1984
- Tongue
- French
- Weight
- 230 KB
- Volume
- 25
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
✦ Synopsis
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. The oxidative conversion of allylic selenides to allylic alcohols (l-,2) is a useful NN synthetic transformation' which proceeds with both high regio-and stereospecificity contrast, the mechanistically analogous oxidative conversion of allylic selenides to amines (l-,3), or derivatives thereof, has remained essentially unexplored,4 despite _Y 3 In sharp allylic the potential synthetic utility of such a procedure.