Synthesis of an octamethyl-18-crown-6 derivative and the X-ray crystal structure of its 2:1 complex with borane-ammonia

David R. Alston*, J. Fraser Stoddart, John B. Wolstenholme, Billy L. Allwood, David J. Williams

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

22 Scopus citations

Abstract

The synthesis of 2,2,3,3,11,11,12,12-octamethyl-1,4,7,10,13,16-hexaoxacyclooctadecane (2) from pinacol (3) by a sequence of reactions (3→4→5→6+5→2) involving alkylation (3→ 4), ozonolysis and reduction (4→5), tosylation (5→6), and cyclisation (5+6→2) is reported. With borane-ammonia, the octamethyl-18-crown-6 derivative 2 forms a crystalline 2:1 complex, (BH3NH3)2 · 2. X-Ray crystallography reveals the two guest BH3NH3 molecules are hydrogen bonded in a centrosymmetric manner to the opposite faces of the host 2, which adopts an all-gauche (ag+a ag-a)3 conformation.

Original languageEnglish (US)
Pages (from-to)2923-2926
Number of pages4
JournalTetrahedron
Volume41
Issue number14
DOIs
StatePublished - 1985

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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