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Published on: March 27, 2019
C12H12 interconversions: two non-pyrolytic syntheses of tricyclo[5.3.2.04,8]dodeca-2,5,9,11-tetraene
Ihsan Erden1, Cindy J Gleason1
1San Francisco State University, Department of Chemistry and Biochemistry, 1600 Holloway Avenue, San Francisco, CA 954132, USA.
Abstract:
Herein, we describe two independent and non-pyrolytic syntheses of an important C12H12 hydrocarbon which had been prepared previously by gas phase thermolysis of compound 6. The first method is based on an unusual dipolar cycloaddition of dichloroketene onto bullvalene. After reductive dechlorination, a Shapiro-Heath reaction of the tosylhydrazone gave the title compound. Alternatively, compound 13 is also obtained from its isomer 6 by a Ag+ catalyzed reaction.
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