C 12 H 12 interconversions: two non-pyrolytic syntheses of tricyclo[5.3.2.0 4,8 ]dodeca-2,5,9,11-tetraene

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 dechlorinatio...

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Bibliographic Details
Published in:Tetrahedron letters 2018-01, Vol.59 (3), p.284
Main Authors: Erden, Ihsan, Gleason, Cindy J
Format: Article
Language:English
Online Access:Get full text
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Summary: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 is also obtained from its isomer by a Ag catalyzed reaction.
ISSN:0040-4039
DOI:10.1016/j.tetlet.2017.12.042