Structure and Reactivity of Small Ring Compounds. IV. Photochemistry of Spirocyclopropyl Ketones

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概要

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• The photochemical transformations of a series of spriocyclopropyl ketones (<B>1</B>–<B>4</B>) have been investigated in dilute <I>n</I>-hexane solutions. Spirocyclopropyl ketones <B>1</B> and <B>2</B> give mainly the 'Type I' photoproducts of cycloalkanones, <I>i.e.</I>, 1-(2′-propenyl)cyclopropanecarboxaldehyde (<B>5</B>, 34%) and 1-(3′-butenyl)cyclopropanecarboxaldehyde (<B>7</B>, 37%), respectively, in marked contrast to the usual photochemical cleavage of cyclopropyl ketones. Ethylidenecycloalkanones are not detected, but their hydrogenated derivatives, 2-ethylcycloalkanones, are produced in a small amount.<BR>The photoreaction of <B>1</B> has been found to be quenched by piperylene, so that it is highly probable that the reaction products are derived from the n-π<SUP>*</SUP> triplet states of the ketones.<BR>The irradiations of nonconjugated spiroketones <B>3</B> and <B>4</B> afford ring-enlarged 4-methylenecycloalkanones, <B>9</B> and <B>10</B>, respectively.

• 公益社団法人 日本化学会の論文

著者

• Tsuji Takashi

  Department Of Biological Science And Technology Faculty Of Industrial Science And Technology Tokyo U

• Sonoda Akio

  Department of Chemistry Faculty of Science Osaka University

• Nishida Shinya

  Department of Chemistry, Faculty of Engineering Science, Osaka University

• Moritani Ichiro

  Department of Chemistry, Faculty of Engineering Science, Osaka University

• Miki Jo

  Department of Chemistry, Faculty of Engineering Science, Osaka University

• Tsuji Takashi

  Department of Chemistry, Faculty of Engineering Science, Osaka University

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