Synthesis and conformation of 3,10-di(t-butyl)- and 3,10-dichloro-4,9-methanothia[11]annulenes

Ryuta Miyatake, Shigeyasu Kuroda*, Takanori Kajioka, Akihide Taketani, Mitsunori Oda

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

3 Scopus citations

Abstract

First two derivatives of 4,9-methanothia[11]annulene, 3,10-di(t-butyl)- and 3,10-dichloro-4,9-methanothia[11]annulenes (4 and 5), were synthesized from the diketosulfide 6. Spectroscopic properties and X-ray crystallographic analyses revealed that 4 exists as an anti-conformer in respect of stereochemical relationship between the methano bridge and the sulfur atom both in solid state and in solution, while 5 exists as a syn-conformer in similarity to the parent of 4,9-methanothia[11]annulene (3).

Original languageEnglish
Pages (from-to)3647-3654
Number of pages8
JournalTetrahedron
Volume58
Issue number19
DOIs
StatePublished - 2002/05/06

Keywords

  • Annulenes
  • Conformation
  • Density functional calculation
  • Heterocycles
  • X-ray crystal structures

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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