One-pot approach to organo phosphorus-chalcogen macrocycles incorporating double OP(S)SCn or OP(Se)SeCn scaffolds: a synthetic and structural study

Guoxiong Hua, Junyi Du, Alexandra M. Z. Slawin, J. Derek Woollins

Research output: Contribution to journalArticlepeer-review

9 Citations (Scopus)

Abstract

The development of new methodology for the preparation of functional macrocycles with practical applications is a fundamental important research area in macromolecular science. In this study, we report a new one-pot route for the synthesis of a series of macro-heterocycles by incorporating two phosphorus atoms and two chalcogen atoms and two oxygen atoms (double OP(S)SCn or OP(Se)SeCn scaffolds). The three-component condensation reactions of 2,4-diferrocenyl-1,3,2,4-diathiadiphosphetane 2,4-disulfide (FcLR, a ferrocene analogue of Lawesson’s reagent) or 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide (LR, Lawesson’s reagent), or 2,4-diphenyl-1,3,2,4-diselenadiphosphetane 2,4-diselenide (WR, Woollins’ reagent), disodium alkenyl-diols, and dihalogenated alkanes are performed giving rise to soluble and air or moisture-stable macrocycloes in good to excellent yields (up to 92%). This is the first systemically preparative and readily scalable example of one-pot ring opening/ring extending reaction of three-components to prepare phosphorus-chalcogen containing macrocycles. We also provide a systematic crystallographic study.
Original languageEnglish
Pages (from-to)7782-7791
Number of pages10
JournalChemistry - A European Journal
Volume22
Issue number23
Early online date26 Apr 2016
DOIs
Publication statusPublished - 1 Jun 2016

Keywords

  • Cyclization
  • Lawesson's reagent
  • Macrocycles
  • Structure elucidation
  • Woollins’ reagent

Fingerprint

Dive into the research topics of 'One-pot approach to organo phosphorus-chalcogen macrocycles incorporating double OP(S)SCn or OP(Se)SeCn scaffolds: a synthetic and structural study'. Together they form a unique fingerprint.

Cite this