Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Reactions of Tropone Tosylhydrazone Sodium Salt with Anthracene, 1,3-Diphenylisobenzofuran, and Phenylacetylene: [2+2] and [4+2] Type Cycloaddition Reactions of Cycloheptatrienylidene or 1,2,4,6-Cycloheptatetraene
Katsuhiro SaitoYoichi OmuraToshio Mukai
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1985 Volume 58 Issue 6 Pages 1663-1668


The reaction of tropone tosylhydrazone sodium salt (1) with anthracene gave a [4+2]-type adduct and the reaction of 1 with 1,3-diphenylisobenzofuran afforded endo- and exo-[4+2]-type adducts as well as a heptafulvene derivative. The reaction of 1 with phenylacetylene yielded a [2+2]-type adduct, which rearranged into 2-phenylindene upon heating. The addition reactions are thought to proceed via the allene intermediate, 1,2,4,6-cycloheptatetraene, which is a valence-bond isomer of the carbene intermediate, cycloheptatrienylidene, initially generated by the pyrolysis of 1. The photoreaction of adduct 3 with a high-pressure mercury lamp afforded a ring-closure product via the photobicyclization reaction of the cycloheptatriene moiety of the adduct. Thermal interconversions between the three products of the reaction of 1 with 1,3-diphenylisobenzofuran were investigated.

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