Optically active cyclic diaryl(alkoxy)sulfonium salts with intramolecular S···O interaction: Synthesis, absolute configuration and stereoselective hydrolysis

Dénes Szabó, Jeno Varga, Antal Csámpai, István Kapovits

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

Optically active cyclic sulfonium salts {(S)-(-)-1-[2'- (methoxycarbonyl)phenyl]-3H-2,1-benzoxathiol-1-ium tetrafluoroborate (S)-(-)- 2, (R)-(-)-1-[8'-(methoxycarbonyl)-1'-naphthyl]-3H-2,1-benzoxathiol-1-ium tetrafluoroborate (R)-(-)-4 and (R)-(-)-1-[2'-(methoxycarbonyl)phenyl]-3H- 2,1-naphtho[1,8-d,e]-oxathiin-1-ium tetrafluoroborate (R)-(-)-6} were prepared from optically active diaryl(acyloxy)(alkoxy)spiro-λ4-sulfanes (R)-(+)-1, (S)-(-)-3 and (S)-(+)-5, respectively. The molecular structures determined by 1H and 13C NMR measurements can be described with spiro- λ4-sulfane-like trigonal bipyramidal geometry about the central sulfur owing to the S···O(carbonyl) intramolecular interaction in the axial position. The stereochemistry of the hydrolysis reactions of sulfonium salts 2, 4, 6 and spiro-λ4-sulfanes 1, 3, 5 depending on pH is discussed in detail. (C) 2000 Elsevier Science Ltd.

Original languageEnglish
Pages (from-to)1303-1312
Number of pages10
JournalTetrahedron Asymmetry
Volume11
Issue number6
DOIs
Publication statusPublished - Apr 7 2000

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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