Azulenesulfonium and azulenebis(sulfonium) salts: Formation by interrupted Pummerer reaction and subsequent derivatisation by nucleophiles

Carlos M. López-Alled, Frederick J.O. Martin, Kuan Yu Chen, Gabriele Kociok-Köhn, Tony D. James, Jannis Wenk, Simon E. Lewis

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Abstract

Azulenes undergo either single or dual SEAr reactions depending on the nature of the sulfur(IV) electrophile employed. These electrophiles are generated in situ from either sulfoxides or sulfides. The resultant cationic or dicationic azulene products can undergo further derivatisation by means of nucleophilic attack at the sulfonium α-carbon. In the case of cycloalkyl azulenylsulfonium salts, this leads to ring-opened azulenylsulfide products.

Original languageEnglish
Article number131700
JournalTetrahedron
Volume76
Issue number49
Early online date22 Oct 2020
DOIs
Publication statusPublished - 4 Dec 2020

Keywords

  • Azulene
  • Interrupted Pummerer
  • Sulfonium

ASJC Scopus subject areas

  • Organic Chemistry

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