Your browser doesn't support javascript.
loading
Preparation, Structure, and Reactivity of Pseudocyclic Benziodoxole Tosylates: New Hypervalent Iodine Oxidants and Electrophiles.
Yoshimura, Akira; Klasen, Scott C; Shea, Michael T; Nguyen, Khiem C; Rohde, Gregory T; Saito, Akio; Postnikov, Pavel S; Yusubov, Mekhman S; Nemykin, Victor N; Zhdankin, Viktor V.
Afiliação
  • Yoshimura A; Department of Chemistry and Biochemistry, University of Minnesota Duluth, MN, 55812, USA.
  • Klasen SC; Department of Chemistry and Biochemistry, University of Minnesota Duluth, MN, 55812, USA.
  • Shea MT; Department of Chemistry and Biochemistry, University of Minnesota Duluth, MN, 55812, USA.
  • Nguyen KC; Department of Chemistry and Biochemistry, University of Minnesota Duluth, MN, 55812, USA.
  • Rohde GT; Department of Chemistry and Biochemistry, University of Minnesota Duluth, MN, 55812, USA.
  • Saito A; Division of Applied Chemistry, Institute of Engineering, Tokyo University of Agriculture and Technology, 2-24-16 Naka-cho, Koganei, Tokyo, 184-8588, Japan.
  • Postnikov PS; The Tomsk Polytechnic University, 634050, Tomsk, Russia.
  • Yusubov MS; The Tomsk Polytechnic University, 634050, Tomsk, Russia.
  • Nemykin VN; Department of Chemistry and Biochemistry, University of Minnesota Duluth, MN, 55812, USA.
  • Zhdankin VV; Department of Chemistry, University of Manitoba, Winnipeg, MB, R3T 2N2, Canada.
Chemistry ; 23(3): 691-695, 2017 01 12.
Article em En | MEDLINE | ID: mdl-27794175
ABSTRACT
New pseudocyclic benziodoxole tosylates were prepared by the treatment of 1-hydroxybenziodoxolones with p-toluenesulfonic acid or via ligand transfer reaction between PhI(OH)OTs (Koser's reagent) and substituted 2-iodobenzoic acids under mild condition. Single crystal X-ray crystallography of these compounds revealed a pseudocyclic structure with a short intramolecular interaction of 2.362 Šbetween oxygen and iodine in the iodoxole ring. Pseudocyclic benziodoxole tosylates readily react with various organic substrates as electrophiles or oxidants to afford the corresponding iodonium salts or the products of oxidation. Furthermore, these compounds can be used as efficient recyclable hypervalent iodine reagents. The reduced form of a pseudocyclic benziodoxole tosylate, 2-iodobenzoic acid, can be efficiently recovered from the reaction mixture by a simple acid-base liquid-liquid biphasic procedure.
Palavras-chave
Texto completo
Imprimir
XML
PubMed Links
Buscar no Google

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Revista: Chemistry Assunto da revista: QUIMICA Ano de publicação: 2017 Tipo de documento: Article País de afiliação: Estados Unidos
Texto completo
Imprimir
XML
PubMed Links
Buscar no Google

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Revista: Chemistry Assunto da revista: QUIMICA Ano de publicação: 2017 Tipo de documento: Article País de afiliação: Estados Unidos