Conversion of mono- and tetra-thiacalix[4]arenes to sulfilimine derivatives and unexpected formation of monospirodienone derivatives

Naoya Morohashi, Makoto Kojima, Akihiro Suzuki, Yoshihiro Ohba

Research output: Contribution to journalArticlepeer-review

8 Citations (Scopus)

Abstract

The treatment of mono- and tetra-thiacalix[4]arenes (2, 3) with chloramine T gave unexpected monospirodienone derivatives (4, 5). The reaction of methyl ethers (6, 7) of thiacalix[4]arenes with chloramine T followed by demethylation gave novel derivatives (10, 11) having a sulfilimine group. X-ray analysis revealed that 11 adopts cone conformation in the solid state, in which the sulfilimine group directs toward axial orientation to take part in circular hydrogen bonding with four OH groups.

Original languageEnglish
Pages (from-to)249-254
Number of pages6
JournalHeterocyclic Communications
Volume11
Issue number3-4
DOIs
Publication statusPublished - 2005
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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