1, 3-Dipolar Cycloadditions. LXXVI. Cycloadditions of Diazomethane to Substituted Butadienes

• HUISGEN ROLF

  Institut fur Organische Chemie der Universitat Munchen

• 太田 明廣

  Institut fur Organische Chemie der Universitat Munchen:(Present address)Tokyo College of Pharmacy

• GEITTNER JOCHEN

  Institut fur Organische Chemie der Universitat Munchen

抄録

1-Substituted butadienes (R=CH₂, CH₃, O, C₃H₅, CO₂CH₃, CN) and 2-phenylbutadiene accept diazomethane at the 3, 4-bond yielding 3-vinylpyrazoline derivatives. Tautomerization of the 1-to 2-pyrazolines takes place either at room temperature (R=CO₂CH₃, CN), on heating (R=C₆H₅) or on acid catalysis (R=H, CH₃, OCH₃) ; the 2-pyrazolines are characterized as 1-carbamoyl and 1-nitroso derivatives. 1-Substituted butadienes follow in their rate constants of diazomethane cycloaddition a linear free energy relationship with Hammett's σp values, ρ=+4.2. The rates and orientations are discussed in the light of the recent MO perturbation treatment.

収録刊行物

• ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ

  ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ 23 (11), 2735-2743, 1975-11-25

  公益社団法人 日本薬学会

キーワード

• Drug Discovery
• General Chemistry
• General Medicine

詳細情報

• CRID: 1390001204172840448
• NII論文ID: 110003621763
• NII書誌ID: AA00602100
• DOI: 10.1248/cpb.23.2735
• ISSN: 13475223
• ISSN: 00092363
• Web Site: https://www.jstage.jst.go.jp/article/cpb1958/23/11/23_11_2735/_pdf
• 本文言語コード: en
• データソース種別:
  • JaLC
  • Crossref
  • CiNii Articles
• 抄録ライセンスフラグ: 使用不可