Journal of Organic Chemistry p. 1643 - 1654 (1983)
Update date:2022-08-04
Topics:
House, Herbert O.
Haack, John L.
McDaniel, William C.
VanDerveer, Don
The bicyclic enones bicyclo<3.2.1>oct-1-en-3-one (4) and 1-methylbicyclo<3.2.1>oct-5(6)-en-7-one (5) have been generated from various precursors and trapped by the addition of nucleophiles such as MeOH, PhSeH, or H2O.The bridgehead enone 5 has also been trapped as its cycloadduct 31 with furan.Pyrolysis of this cycloadduct 31 reformed the bridgehead enone 5 that was trapped as the cycloadduct 32.Related bridgehead enones 35 and 47 have also been generated as intermediates leading to products with bridgehead methoxy substituents.
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