Photochemistry of heterocyclic compounds. VII. Photochemical reaction of 2,5-diphenyl-1,3,4-oxadiazole with benzo[b]thiophenes.
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概要
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Irradiation of 2,5-diphenyloxadiazole <B>1</B> with benzothiophene <B>6a</B> gives 3-benzoylbenzothiophene <B>7</B>, its benzoylhydrazone <B>8</B>, and/or the oxadiazepine <B>9</B>; the yields depended on the nature of solvents. With benzophenone as a sensitizer, the photochemical reaction of <B>1</B> with <B>6a</B> forms the [2+2] cycloadduct <B>12</B>. It is found that <B>9</B> is photochemically dissociated to <B>1</B> and <B>6a</B>. In the case of 2-methylbenzothiophene <B>6b</B>, 3-benzoyl-2-methylbenzothiophene benzoylhydrazone <B>18</B> is formed, and with benzophenone as a sensitizer the [2+2] cycloadduct <B>19</B> is obtained. In the absence or presence of benzophenone, however, irradiation of <B>1</B> with 3-methylbenzothiophene <B>6c</B> gives the [2+2] cycloadduct <B>20</B>. The photochemical reaction of <B>1</B> with <B>6a</B> or <B>6b</B> in the presence of iodine gives the corresponding 3-benzoylbenzothiophene, <B>7</B> or <B>21</B>, and benzoylhydrazone, <B>8</B> or <B>18</B>, respectively. In the case of <B>6c</B>, however, the [2+2] cycloadduct <B>23</B> is formed, together with 2-benzoyl-3-methylbenzothiophene <B>22</B>. Mechanistic considerations of these reactions are also described.
- 公益社団法人 日本化学会の論文
著者
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Tsuge Otohiko
Research Institute of Industrial Science, and Department of Molecular Science and Technology, Interdisciplinary Graduate School of Engineering Sciences Kyushu University
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Tashiro Masashi
Research Institute of Industrial Science, and Department of Molecular Science and Technology, Graduate School of Engineering Sciences, Kyushu University 86
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Oe Koji
Research Institute of Industrial Science, Kyushu University 86
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