Nitroalkenylferrocene. V. New Reactions of α-Halonitroolefins in the Presence of Sodium Alkoxides

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概要

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• The reactions of 1-iodo-2-ferrocenyl-1-nitroethylene (<B>1</B>) and β-bromo-β-nitrostyrene (<B>5</B>) with various sodium alkoxides were investigated. The reaction in the presence of an excess of alkoxides gave nitroketones, (<B>2</B>) and (<B>6</B>), and nitroacetals (<B>3</B>) and (<B>7</B>). The thermal decomposition of the nitroacetals in a nitrogen atmosphere afforded β-alkoxynitroolefins (<B>8</B>), which were found to be useful for obtaining asymmetric nitroacetals (<B>9</B>) with different alkoxy groups. The reaction mechanism was discussed by postulating the intervention of a nitrocarbene (<B>12</B>) and β-alkoxynitroolefin (<B>8</B>). The intermediacy of the nitrocarbene was supported by an experiment using vinylferrocene as a carbene scavenger.

• 公益社団法人 日本化学会の論文

著者

• Motoyama Izumi

  Department Of Applied Chemistry Faculty Of Engineering Kanagawa University

• Hata Kazuo

  Department of Chemistry, Faculty of Science, Tokyo Metropolitan University

• Kono Hiromichi

  Department of Chemistry, Faculty of Science, Tokyo Metropolitan University

• Shiga Mikio

  Department of Chemistry, Faculty of Science, Tokyo Metropolitan University

• Tsunashima Masaaki

  Department of Chemistry, Faculty of Science, Tokyo Metropolitan University

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