Exciton coupling in the CD spectra of chiral spiro-λ4-sulfanes and related sulfoniumn salts

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

Enantiomers of spiro-λ4-sulfanes 2-7 and related cyclic sulfonium salts 2c-7c have been obtained by stereo-specific synthesis. Exciton splitting was observed in the CD spectra of spiro-λ4-sulfanes and sulfonium salts having both benzene and napthalene-benzene rings. The absolute configurations were deduced from the sign of the couplet. Exciton couplets in the CD spectra of sulfonium salts and their parent λ4-sulfanes show the same sign which follows from the same orientation of the coupled electric transition moments due to their similar trigonal bipyramidal geometry. Based on the known stereomechanism of the formation of spiro-λ4-sulfanes and sulfonium salts as well as of their hydrolysis leading to the corresponding sulfoxides (2a-7a and 2b-7b), the absolute configurations of sulfoxides could also be deduced from the sign of exciton couplet in the CD spectra of related λ4-sulfanes and sulfonium salts.

Original languageEnglish
Pages (from-to)513-520
Number of pages8
JournalEnantiomer
Volume5
Issue number5
Publication statusPublished - 2000

Fingerprint

Salts
Sulfoxides
Benzene
Enantiomers
Hydrolysis
LDS 751
Geometry

Keywords

  • Absolute configuration
  • Circular dichroism
  • Spiro-λ-sulfanes
  • Sulfonium salts
  • Sulfoxides

ASJC Scopus subject areas

  • Chemistry(all)
  • Organic Chemistry
  • Biochemistry, Genetics and Molecular Biology(all)
  • Biochemistry

Cite this

Exciton coupling in the CD spectra of chiral spiro-λ4-sulfanes and related sulfoniumn salts. / Varga, J.; Szabó, D.; Hollósi, M.

In: Enantiomer, Vol. 5, No. 5, 2000, p. 513-520.

Research output: Contribution to journalArticle

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AU - Hollósi, M.

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N2 - Enantiomers of spiro-λ4-sulfanes 2-7 and related cyclic sulfonium salts 2c-7c have been obtained by stereo-specific synthesis. Exciton splitting was observed in the CD spectra of spiro-λ4-sulfanes and sulfonium salts having both benzene and napthalene-benzene rings. The absolute configurations were deduced from the sign of the couplet. Exciton couplets in the CD spectra of sulfonium salts and their parent λ4-sulfanes show the same sign which follows from the same orientation of the coupled electric transition moments due to their similar trigonal bipyramidal geometry. Based on the known stereomechanism of the formation of spiro-λ4-sulfanes and sulfonium salts as well as of their hydrolysis leading to the corresponding sulfoxides (2a-7a and 2b-7b), the absolute configurations of sulfoxides could also be deduced from the sign of exciton couplet in the CD spectra of related λ4-sulfanes and sulfonium salts.

AB - Enantiomers of spiro-λ4-sulfanes 2-7 and related cyclic sulfonium salts 2c-7c have been obtained by stereo-specific synthesis. Exciton splitting was observed in the CD spectra of spiro-λ4-sulfanes and sulfonium salts having both benzene and napthalene-benzene rings. The absolute configurations were deduced from the sign of the couplet. Exciton couplets in the CD spectra of sulfonium salts and their parent λ4-sulfanes show the same sign which follows from the same orientation of the coupled electric transition moments due to their similar trigonal bipyramidal geometry. Based on the known stereomechanism of the formation of spiro-λ4-sulfanes and sulfonium salts as well as of their hydrolysis leading to the corresponding sulfoxides (2a-7a and 2b-7b), the absolute configurations of sulfoxides could also be deduced from the sign of exciton couplet in the CD spectra of related λ4-sulfanes and sulfonium salts.

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