The Photochemical Decomposition of Benzenediazonium <I>o</I>-Carboxylate in Several Solvents

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概要

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• The photochemical decompositions of benzenediazonium <I>o</I>-carboxylate (<B>1</B>) in water, ethanol, acetone, and dichloromethane were studied. In every case, the initial loss of molecular nitrogen to give a zwitterion (<B>3</B>) and/or a diradical (<B>4</B>) was the primary process. In the solvents which are susceptible to hydrogen abstraction by a radical (ethanol and acetone), reduction takes place to give benzoic acid, through <B>4</B>, in a good yield. In water, from which a hydrogen atom is less easily abstracted homolytically, salicylic acid was the main product (24%), while benzoic acid was the minor one (9%). In CH<SUB>2</SUB>Cl<SUB>2</SUB>, the reduction product (benzoic acid, 20%) and biphenylene (10%) were formed. The formation of the latter compound prompted us to study the photochemical decomposition of <B>1</B> in CH<SUB>2</SUB>Cl<SUB>2</SUB> in the presence of tropone. This reaction gave cycloaddition products, (<B>11</B>) and (<B>12</B>), in 3.2 and 0.7% yields respectively.

• 公益社団法人 日本化学会の論文

著者

• Kato Masahiko

  Faculty Of Engineering Hiroshima University

• Miwa Toshio

  Faculty of Science, Osaka City University

• Tamano Taizo

  Faculty of Science, Osaka City University

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