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Alumina-Catalyzed Cope Rearrangement, Paul Jhy-Shing Wang
Alumina-Catalyzed Cope Rearrangement, Paul Jhy-Shing Wang
Dissertations and Theses
The alumina-catalyzed Cope rearrangements of meso- and dl-3,4-diphenylhexa-1,5-diene were examined in detail, following up a preliminary observation by H. Berg at Portland State University. Commercial column-chromatography grade alumina was employed, and was further activated before use by heating at 650-700° for four hours.
Using a ratio of 20 mg of dl-3,4-diphenylhex-l,5-diene to 1 g of alumina in heptane, the Cope rearrangement was complete within 15 minutes at room temperature to give exclusively trans,trans-1,6-diphenylhexa-1,5-diene. This was identified.by melting point, infrared spectroscopy and vapor phase chromatography.
The catalyzed rearrangement of meso-3,4-diphenylhexa-l,5-diene was run using the same diene …