Solvolysis of 1-[trans-2-(m- or p-Substituted Phenyl)cyclopropyl]-1-methylethyl p-Nitrobenzoates

• Yoshiaki Kusuyama

書誌事項

タイトル別名

• Solvolysis of 1 trans 2 m or p-Substitu

抄録

The solvolyses of 1-[trans-2-(m- or p-substituted phenyl)cyclopropyl]-1-methylethyl p-nitrobenzoates in 80% aqueous acetone have been studied with regard to both reactivity and product composition. For the less reactive substituents such as m-Br, m-Cl, and m-CF3, the solvolysis products were the corresponding 2-(2-arylcyclopropyl)-2-propanol, indicating the cyclopropylmethyl cation intermediate. The ring-opened products increased as the electron-donating ability of the substituents increased. The application of the Yukawa–Tsuno equation to the reactivity afforded a ρ value of −1.43 and r value of 0.59 with a correlation coefficient of 0.997. A large value of r indicates the presence of the allylic cation intermediate where much more charge develops at the benzylic carbon for the derivatives with electron-donating substituents than is the case for the cyclopropylmethyl cation intermediate. Thus the solvolysis reaction proceeds via two independent pathways: one has a cyclopropyl cation intermediate and the other has a homoallylic cation intermediate.

収録刊行物

• Bulletin of the Chemical Society of Japan

  Bulletin of the Chemical Society of Japan 71 (3), 685-691, 1998-03

  Tokyo : Chemical Society of Japan

キーワード

• General Chemistry

詳細情報

• CRID: 1521699229767694080
• NII論文ID: 10008929907
• NII書誌ID: AA00580132
• ISSN: 00092673
• ISSN: 13480634
• DOI: 10.1246/bcsj.71.685
• NDL書誌ID: 4440384
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I4440384
• Web Site: https://academic.oup.com/bcsj/article-pdf/71/3/685/56195270/bcsj.71.685.pdf
• 本文言語コード: en
• NDL 雑誌分類:
  • ZP1(科学技術--化学・化学工業)
• データソース種別:
  • NDL
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