The chemistry of substituted norbornenes. Reactions of 5-vinyl-2-norbornene and 5-ethylidene-2-norbornene with formic acid.
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概要
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Addition of formic acid to 5-vinyl-2-norbornene(<B>1</B>) and subsequent hydrolysis afford 6-vinyl-<I>exo</I>-2-norbornanol(<B>5</B>) and 5-vinyl-<I>exo</I>-2-norbornanol(<B>6</B>). Similarly, from 5-ethylidene-2-norbornene(<B>2</B>) are formed 6-ethylidene-<I>exo</I>-2-norbornanol(<B>14</B>), 5-ethylidene-<I>exo</I>-2-norbornanol(<B>15</B>), and 6-ethyltricyclo[2.2.1.0<SUP>2,6</SUP>]heptan-3-ol(<B>16</B>). The hydroboration of <B>2</B> also leads to the formation of <B>14</B> and <B>15</B>. Thus, the vinyl- and ethylidene-<I>exo</I>-norbornanols, <B>5</B>, <B>6</B>, <B>14</B>, and <B>15</B>, and the corresponding <I>endo</I>-norbornanols, <B>9</B>, <B>10</B>, <B>21</B>, and <B>22</B>, have been synthesized. A structural analysis of these products by <SUP>13</SUP>C NMR revealed that under certain conditions, the ethylidene group of <B>2</B> exerts a great influence upon the reactivity of the norbornenyl ring double bond. Moreover, the fact that <B>16</B> derived from the addition of formic acid to <B>2</B> consists of both <I>exo</I>- and <I>endo</I>-hydroxy epimers is inconsistent with the previous observations that the <I>exo</I>-isomer is generally the sole product in related systems.
- 公益社団法人 日本化学会の論文
著者
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Inoue Yoshiharu
Research Institute For Food S-cience Kyoto University
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TANIMOTO Fumio
Research Institute for Production Development
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Tanimoto Fumio
Research Institute for Production Development, 15
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Kitano Hisao
Research Institute for Production Development, 15
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