Solvolysis of (4,5)-anti-4-Aryl-5-tosyloxy-2(E)-hexenoate Derivatives

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概要

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• The solvolysis reaction of (4,5)-anti-4-aryl-5-tosyloxy-2(E)-hexenoates 4a-k gave (4, 5)-anti-4-aryl-5-hydroxy-2(E)-hexenoates 2a-k and (4,5)-anti-5-aryl-4-hydroxy-2(E)-hexenoates 5a-k along with the complete inversion. This 1,2-aryl migration was induced by treatment with heating in water-saturated nitromethane. On the basis of the substituent effect on the aromatic ring, this 1,2-aryl migration is thought to proceed via the σ-bridged phenonium ion. The product selectivity between 2a-k and 5a-k was found to be subtly governed by the substituent and substitution pattern in the aromatic ring of the substrates 4a-k.

• 公益社団法人日本薬学会の論文
• 2005-10-01

著者

• AKITA Hiroyuki

  School of Pharmaceutical Science, Toho University

• Akita H

  Toho Univ. Chiba Jpn

• Akita Hiroyuki

  School Of Pharmaceutical Science Toho University

• ONO Machiko

  School of Pharmaceutical Sciences, Toho University

• Akita Hiroyuki

  School Of Parmaceutical Sciences Toho University

• EHARA Takeru

  School of Pharmaceutical Sciences, Toho University

• YOKOYAMA Hirofumi

  School of Pharmaceutical Sciences, Toho University

• OHTANI Nobuyoshi

  School of Pharmaceutical Sciences, Toho University

• HOSHINO Youko

  School of Pharmaceutical Sciences, Toho University

• Ehara Takeru

  School Of Pharmaceutical Sciences Toho University:tsukuba Research Institute Novartis Pharma K.k.

• Hoshino Youko

  School Of Pharmaceutical Sciences Toho University

• Ono M

  School Of Pharmaceutical Sciences International University Of Health And Welfare

• Ono Machiko

  School Of Pharmaceutical Sciences Toho University

• Ohtani Nobuyoshi

  School Of Pharmaceutical Sciences Toho University

• Ono Machiko

  School Of Pharmaceutical Sciences International Univ. Of Health And Welfare

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