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- Title
Carboboration Reactions of 1,2-Bis[(diarylphosphino)ethynyl]benzenes with Tris(pentafluorophenyl)borane.
- Authors
Liedtke, René; Kehr, Gerald; Fröhlich, Roland; Daniliuc, Constantin G.; Wibbeling, Birgit; Petersen, Jeffrey L.; Erker, Gerhard
- Abstract
The 1,2-bis[(diarylphosphino)ethynyl]benzene derivatives 1a (R=Ph) and 1b (R= o-tolyl) undergo 1,1-carboboration at one of their acetylene units upon treatment with (C6F5)3B at elevated temperature to give the products 5a and 5b, respectively. At room temperature, we observed the formation of the corresponding phosphireniumborate zwitterions, 7a and 7b, respectively, which may be intermediates of the 1,1-carboboration reactions. The reaction of the more bulky 1,2-bis[(dimesitylphosphino)ethynyl]benzene 1c with (C6F5)3B takes a different course. At 110°, we observed the complete conversion to the benzopentafulvene derivative 8 which is probably formed in a typical carbocation rearrangement sequence after the initial (C6F5)3B Lewis acid-addition step. The compounds 5a, 5b, 7b, and 8 were characterized by X-ray crystal-structure analyses.
- Subjects
BENZENE derivatives; HIGH temperatures; ACETYLENE; CARBOCATIONS; CATIONS
- Publication
Helvetica Chimica Acta, 2012, Vol 95, Issue 12, p2515
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.201200495