Conformational effect on the bridgehead reaction of bicylco[3.3.1]nonan-2-ones. A facile bridgehead deuteration of a bicyclo[3.3.1]nonan-2-one derivative with the cyclohexanone ring locked in the boat conformation.

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概要

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• Five bicyclo[3.3.1]nonan-2-ones, two known (<B>1</B>, <B>3</B>) and three new ones (<B>2</B>, <B>4</B>, <B>5</B>) were prepared. The hydrogen-deuterium exchange reaction at the bridgehead position of the bicyclo[3.3.1]nonan-2-one system was examined under mild basic conditions (2 M NaOMe-MeOD, 33 °C, 22 h) using these five bicyclo[3.3.1]nonan-2-ones. Virtually no deuteration took place at the bridgehead in each case of the bicyclic ketones (<B>1</B>, <B>2</B>, <B>3</B>, <B>4</B>), whereas one deuterium was incorporated into the bridgehead of the ketone (<B>5</B>). <SUP>13</SUP>C NMR spectroscopy was employed for the unambiguous determination of the site(s) of deuteration in all cases studied. The enhanced bridgehead acidity of (<B>5</B>) could be explained in terms of the locked boat conformation of the cyclohexanone ring contained in (<B>5</B>).

• 公益社団法人 日本化学会の論文

著者

• Suzuki Masaaki

  Department Of Atherosclerosis Metabolism And Clinical Nutrition National Cardiovascular Center

• Yamada Kiyoyuki

  Department Of Chemistry Faculty Of Science Nagoya University

• Manabe Shunichi

  Department of Chemistry, Faculty of Science, Nagoya University

• Kyotani Yoshinori

  Department of Chemistry, Faculty of Science, Nagoya University

• Hirata Yoshimasa

  Department of Chemistry, Faculty of Science, Nagoya University

• Suzuki Masaaki

  Department of Chemistry, Faculty of Science, Nagoya University

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