Synthesis and X-ray structures of iodothiacalix[4]arenes

Shinya Tanaka, Hiroshi Katagiri, Naoya Morohashi, Tetsutaro Hattori, Sotaro Miyano

Research output: Contribution to journalArticlepeer-review

11 Citations (Scopus)

Abstract

Mono-, di-, and tetraiodothiacalix[4]arenes 13-16 have been successfully synthesized for the first time by the Griess reaction of diazonium salts of the corresponding aminothiacalix[4]arenes 4-7. X-ray crystallography reveals that monoiodinated compound 13 adopts a distorted pinched cone conformation, in which the three hydroxy groups and the iodine atom form a pseudo-cyclic hydrogen bonding. On the other hand, tetraiodinated compound 16 adopts a 1,3-alternate conformation presumably due to the steric hindrance and dipole repulsion between the iodine atoms.

Original languageEnglish
Pages (from-to)5293-5296
Number of pages4
JournalTetrahedron Letters
Volume48
Issue number30
DOIs
Publication statusPublished - 2007 Jul 23

Keywords

  • Amination
  • Calixarene
  • Griess reaction
  • Nucleophilic aromatic substitution

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Synthesis and X-ray structures of iodothiacalix[4]arenes'. Together they form a unique fingerprint.

Cite this