Journal of Organic Chemistry p. 2033 - 2039 (1982)
Update date:2022-08-04
Topics:
Freeman, Peter K.
Swenson, Karl E.
Pyrolytic decomposition of the lithium or potassium salt of the tosylhydrazone of bicyclo<3.2.1>octa-3,6-dien-2-one (11) or photolysis of the lithium salt of 11 results in the formation of bicyclo<3.2.1>octa-2,6-diene (12), tricyclo<3.2.1.02,7>oct-3-ene (13), tetracyclo<3.3.0.02,8.04,6>octane (14), semibullvalene (15), 5-ethynyl-1,3-cyclohexadiene (16), and endo-6-ethynylbicyclo<3.1.0>hex-2-ene (17).The formation of the C8H8 fraction (15-17) is ascribed to insertion and rearrangement reactions of singlet 2-carbenabicyclo<3.2.1>octadiene, whereas the formation ofthe C8H10 fraction (12-14) appears to be the result of hydrogen abstraction reactions of the corresponding triplet carbene or closely related species.
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