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

Citation
D. Crich et al., Design, synthesis, application and recovery of a minimally fluorous diaryldiselenide for the catalysis of stannane-mediated radical chain reactions, TETRAHEDRON, 55(50), 1999, pp. 14261-14268
Citations number
37
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
55
Issue
50
Year of publication
1999
Pages
14261 - 14268
Database
ISI
SICI code
0040-4020(199912)55:50<14261:DSAARO>2.0.ZU;2-M
Abstract
The synthesis of a minimally fluorous (52% F) diaryl diselenide is describe d. On reduction in situ with tributylstannane this diselenide provides a fl uorous selenol which is effective in inhibiting a range of stannane-mediate d radical rearrangements, including a cyclopropylcarbinyl ring opening. A m ethod for the recovery of the fluorous diselenide involving continuous extr action in a modified, cooled continuous extractor is described. (C) 1999 El sevier Science Ltd. All rights reserved.