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Stereo- and regioselective halogenation of norbornenes directed by neighboring group participation.
- Source :
-
Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry . Dec2016, Vol. 57 Issue 50, p5584-5587. 4p. - Publication Year :
- 2016
-
Abstract
- Directing the outcome of electrophilic addition reactions of norbornenes could be a challenging task. We have found that the ionic addition of bromine to dichloro-norbornene 2 is accompanied with the formation of a bromonium cation followed by anchimeric assistance of juxtaposed chlorine to give five-membered chloronium cation, which upon reacting with bromide gives norbornane 4 in >90% yield. At higher temperatures, however, the radical addition of Br 2 dominates so that dibromo compound 3 appears as the principal reaction product (72%). Stereo- and regioselective rearrangements of norbornenes, reported herein, could be of interest for the syntheses of complex haloalkanes. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 00404039
- Volume :
- 57
- Issue :
- 50
- Database :
- Academic Search Index
- Journal :
- Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 119581812
- Full Text :
- https://doi.org/10.1016/j.tetlet.2016.10.105