The preparation of photoresponsive cyclobutanocrown ethers by means of intramolecular [2+2]photocycloaddition.

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概要

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• The reaction of <I>o</I>-bis(3-hydroxy-1-oxapropyl)benzene (<B>7b</B>) with 3,3′-(trimethylenedi-4,1-phenylene)bis[2-propenoyl chloride] gave 8,9-benzo-4,7,10,13-tetraoxa[16.3]paracyclopha-1,8,15-triene-3,14-dione (<B>8b</B>) in a 6.5% yield, together with its dimer in a 12.3% yield. Also, 5,6-benzo-4,7-dioxa[10.3]paracyclopha-1,5,9-triene-3,8-dione (<B>8a</B>) and 11,12-benzo-4,7,10,13,16,19-hexaoxa[22.3]paracyclopha-1,11,21-triene-3,20-dione (<B>8c</B>) were obtained by the same method in 7.0 and 8.0% yields, together with their respective dimers (<B>9a</B>: 6.0%, <B>9c</B>: 10.8%). X-Ray analysis of <B>8b</B> revealed the two double bonds to be trans and the distances between the two olefinic carbon atoms (C<SUB>17</SUB>–C<SUB>35</SUB>) and (C<SUB>18</SUB>–C<SUB>34</SUB>) to be 5.341(11) and 5.906(9) Å respectively. These distances are too long for intramolecular [2+2]photocycloaddition to occur in the crystalline state. However, the irradiation of the solutions of the crown ethers <B>8a</B> and <B>8b</B> in acetonitrile by Pyrex-filtered UV light (>300nm) gave two intramolecular [2+2]photocycloadducts, cyclobutanocrown ethers <B>10a</B> and <B>10b</B>, in 95.7 and 91.8% yields respectively. Subsequently, <B>10a</B> and <B>10b</B> were transformed to <B>8a</B> and <B>8b</B> in 37 and 29% yields respectively upon irradiation with 220 nm UV light. The structures of <B>10a</B> and <B>10b</B> were confirmed to be the β-form.

• 公益社団法人 日本化学会の論文

著者

• Akabori Sadatoshi

  Department Of Chemistry Faculty Of Science Toho University

• Sato Sadao

  Analytical And Metabolic Research Laboratories Sankyo Co. Ltd.

• Kumagai Takeshi

  Department Of Electrical Engineering Nagaoka University Of Technology

• Habata Yoichi

  Department of Chemistry, Faculty of Science, Toho University

• Kumagai Takeshi

  Department of Chemistry, Faculty of Science, Toho University

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