Enones with Strained Double Bonds. 10. Use of Flash Vacuum Pyrolysis To Obtain Bicyclonon-1-en-3-one

Article abstract of DOI:10.1021/jo00388a024

Pyrolysis of the furan adducts 3 in the gas phase at low pressure (10^-4 mm) formed a mixture of furan and the bicyclic enone 2a with a bridgehead double bond that could be collected in a cold trap.NMR, IR, and UV spectra of this mixture were obtained.Although the enone 2a reacted rapidly with methanol and more slowly with furan, efforts to find products from the reaction of the enone 2a with either ground-state oxygen or one of several unsaturated compounds 9,11,12, or 13 were unsuccessful.Instead, at temperatures above -40 deg C the enone 2a reacted with itself to form a mixture of the three dimers 4a, 4b, and 4c.