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

✍ Scribed by Dénes Szabó; Szilárd Szendeffy; István Kapovits; Árpád Kucsman; Gyula Argay; Alajos Kálmán; László Párkányi

Book ID
104361260
Publisher
Elsevier Science
Year
1997
Tongue
English
Weight
520 KB
Volume
8
Category
Article
ISSN
0957-4166

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✦ Synopsis

The spiro-?k4-sulfane (spirosulfurane) precursors 2-[(2-hydroxymethylphenyl)sulfinyl]benzoic acid 1, 8-[(2-hydroxymethylphenyl)sulfinyl]-l-naphthoic acid 2, and 2-[(8-hydroxymethyl-l-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.

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Stereospecific synthesis and absolute configuration of optically active diaryl(acyloxy)(alkoxy)spiro-λ4-sulfanes
✍ Dénes Szabó; Szilárd Szendeffy; István Kapovits; Árpád Kucsman; Mátyás Czugler; 📂 Article 📅 1997 🏛 Elsevier Science 🌐 English ⚖ 601 KB

Optically active (R)-(+)-l,l '-spirobi[3H-2,1-benzoxathiol]-3-one (R)-(+)-5, the (R)-(+) and (S)-(-) enantiomers of spiro [3H-2,1-benzoxathiol-l,l'-naphtho[1,8-d,e]-3H-2,1-oxathiin-3-one] (R)-(+)-8 and (S)-(-)-8, and (S)-(+)-spiro [3H-2,l-benzoxathiol-3-one-l,l'-naphtho[1,8-d,e]-3H-2,1-oxathiine] (S