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.

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概要

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• The reaction of tropone tosylhydrazone sodium salt (<B>1</B>) with anthracene gave a [4+2]-type adduct and the reaction of <B>1</B> with 1,3-diphenylisobenzofuran afforded <I>endo</I>- and <I>exo</I>-[4+2]-type adducts as well as a heptafulvene derivative. The reaction of <B>1</B> with phenylacetylene yielded a [2+2]-type adduct, which rearranged into 2-phenylindene upon heating. The addition reactions are thought to proceed <I>via</I> 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 <B>1</B>. The photoreaction of adduct <B>3</B> with a high-pressure mercury lamp afforded a ring-closure product <I>via</I> the photobicyclization reaction of the cycloheptatriene moiety of the adduct. Thermal interconversions between the three products of the reaction of <B>1</B> with 1,3-diphenylisobenzofuran were investigated.

• 公益社団法人 日本化学会の論文

著者

• Saito Katsuhiro

  Department Of Agricultural And Resource Economics The University Of Tokyo

• Mukai Toshio

  Department of Chemistry, Faculty of Science, Tohoku University

• Omura Yoichi

  Department of Chemistry, Nagoya Institute of Technology

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