Products from the nitration of 2,5-dimethylthiophene and its 3,4-dibromo derivative. Two modes of the formation of dithienylmethanes.

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概要

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• The reaction of 2,5-dimethylthiophene with copper(II) nitrate in acetic anhydride gave 3-nitro-2,5-dimethyl-thiophene and 2,5-dimethyl-3-(5-methyl-2-thenyl)thiophene as major isolable products. The treatment of 3,4-dibromo-2,5-dimethylthiophene with nitric acid (<I>d</I>=1.5) in dichloromethane in the presence of a catalytic amount of sulfuric acid afforded 3,4-dibromo-5-methyl-2-(nitrooxymethyl)thiophene, which, on thin-layer chromatog-raphy over silica gel using hexane as the eluant, underwent a partial novel coupling reaction through the loss of one methylene carbon atom, thus giving 3,3′,4,4′-tetrabromo-5,5′-dimethyldi-2-thienylmethane along with the expected 3,4-dibromo-2-hydroxymethyl-5-methylthiophene and bis(3,4-dibromo-5-methyl-2-thenyl) ether.

• 公益社団法人 日本化学会の論文

著者

• Hidaka Ichiro

  Department Of Cardiovascular Dynamics National Cardiovascular Center Research Institute

• Suzuki Hitomi

  Deparment Of Chemistry School Of Science Kwansei Gakuin University

• Osuka Atsuhiro

  Department Of Chemistry Faculty Of Science Kyoto University

• Hidaka Ichiro

  Department of Chemistry, Faculty of Science, Ehime University

• Iwasa Akemi

  Department of Chemistry, Faculty of Science, Hiroshima University

• Mishina Tadashi

  Department of Chemistry, Faculty of Science, Hiroshima University

• Mishina Tadashi

  Department of Chemistry, Faculty of Science, Ehime University

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