Resolution and absolute configuration of enantiomeric spiro-λ4-sulfane-precursor diaryl sulfoxides

D. Szabó, Szilárd Szendeffy, István Kapovits, Árpád Kucsman, G. Argay, A. Kálmán, L. Párkányí

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

The spiro-λ4-sulfane (spirosulfurane) precursors 2-[(2-hydroxymethylphenyl)-sulfinyl]benzoic acid 1, 8-[(2-hydroxymethylphenyl)sulfinyl]-1-naphthoic acid 2, and 2-[(8-hydroxymethyl-1-naphthyl)sulfinyl]benzoic acid 3 were prepared from the corresponding sulfides by oxidation with chloramine-T. By using chiral organic bases racemic 1-3 were resolved to yield the enantiomers in high enantiomeric excess. The molecular structures of sulfoxides (+)-1, (+)-2, and (+)-3 were determined by X-ray diffraction method, and the absolute configuration of the stereogenic sulfur atom was assigned as (R), (S), and (S), respectively. The actual conformations are discussed including effective S···O close contacts and the relative positions of aromatic rings. Relevant bond lengths, angles and CD spectra are also given.

Original languageEnglish
Pages (from-to)2403-2410
Number of pages8
JournalTetrahedron Asymmetry
Volume8
Issue number14
DOIs
Publication statusPublished - Jul 24 1997

Fingerprint

Sulfoxides
Benzoic Acid
Benzoic acid
benzoic acid
Enantiomers
enantiomers
Bond length
Sulfides
configurations
Molecular Structure
Sulfur
X-Ray Diffraction
Molecular structure
Conformations
sulfides
molecular structure
sulfur
X ray diffraction
Atoms
Oxidation

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Organic Chemistry
  • Materials Chemistry
  • Drug Discovery

Cite this

Resolution and absolute configuration of enantiomeric spiro-λ4-sulfane-precursor diaryl sulfoxides. / Szabó, D.; Szendeffy, Szilárd; Kapovits, István; Kucsman, Árpád; Argay, G.; Kálmán, A.; Párkányí, L.

In: Tetrahedron Asymmetry, Vol. 8, No. 14, 24.07.1997, p. 2403-2410.

Research output: Contribution to journalArticle

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AU - Szendeffy, Szilárd

AU - Kapovits, István

AU - Kucsman, Árpád

AU - Argay, G.

AU - Kálmán, A.

AU - Párkányí, L.

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