Tetrahedron

Design, synthesis, application and recovery of a minimally fluorous diaryl diselenide for the catalysis of stannane-mediated radical chain reactions

D Crich, X Hao, M Lucas

Index: Crich, David; Xiaolin, Hao; Lucas, Mathew Tetrahedron, 1999 , vol. 55, # 50 p. 14261 - 14268

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Citation Number: 49

Abstract

The synthesis of a minimally fluorous (52% F) diaryl diselenide is described. On reduction in situ with tributylstannane this diselenide provides a fluorous selenol which is effective in inhibiting a range of stannane-mediated radical rearrangements, including a cyclopropylcarbinyl ring opening. A method for the recovery of the fluorous diselenide involving continuous extraction in a modified, cooled continuous extractor is described.