Resolution and Determination of the Absolute Configuration of the Enantiomers of a trans-alpha-Disulfoxide

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Resolution and Determination of the Absolute Configuration of the Enantiomers of a trans-alpha-Disulfoxide. / Allenmark, S; Grainger, Richard; Olsson, S; Patel, B.

In: European Journal of Organic Chemistry, No. 22, 01.08.2011, p. 4089-4092.

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@article{806900e6f8c14c17869bf5887babd4c1,
title = "Resolution and Determination of the Absolute Configuration of the Enantiomers of a trans-alpha-Disulfoxide",
abstract = "The trans isomer of 2,7-di-tert-butylnaphtho[1,8-cd][1,2]dithiole 1,2-dioxide, a vic-disulfoxide of the highest thermal stability reported to date, has been resolved into its enantiomers by preparative chiral liquid chromatography. This represents the first resolution achieved of a vic-disulfoxide. The absolute configuration of the isolated enantiomers has been determined to be (+)-(S,S), (-)-(R,R) from a comparison of experimental and calculated ECD and VCD spectra. The long-wavelength ECD band at about 330 nm had a positive sign in the (+)-(S,S)-form and a negative sign in the (-)-(R,R)-enantiomer. A photocatalyzed slow decrease in optical activity was observed in solution, most likely due to racemization by homolytic (O)S-S(O) bond cleavage and bissulfinyl radical recombination.",
keywords = "Sulfur, Circular dichroism, Density functional calculations, Configuration determination",
author = "S Allenmark and Richard Grainger and S Olsson and B Patel",
year = "2011",
month = aug,
day = "1",
doi = "10.1002/ejoc.201100419",
language = "English",
pages = "4089--4092",
journal = "European Journal of Organic Chemistry",
issn = "1434-193X",
publisher = "Wiley-VCH Verlag",
number = "22",

}

RIS

TY - JOUR

T1 - Resolution and Determination of the Absolute Configuration of the Enantiomers of a trans-alpha-Disulfoxide

AU - Allenmark, S

AU - Grainger, Richard

AU - Olsson, S

AU - Patel, B

PY - 2011/8/1

Y1 - 2011/8/1

N2 - The trans isomer of 2,7-di-tert-butylnaphtho[1,8-cd][1,2]dithiole 1,2-dioxide, a vic-disulfoxide of the highest thermal stability reported to date, has been resolved into its enantiomers by preparative chiral liquid chromatography. This represents the first resolution achieved of a vic-disulfoxide. The absolute configuration of the isolated enantiomers has been determined to be (+)-(S,S), (-)-(R,R) from a comparison of experimental and calculated ECD and VCD spectra. The long-wavelength ECD band at about 330 nm had a positive sign in the (+)-(S,S)-form and a negative sign in the (-)-(R,R)-enantiomer. A photocatalyzed slow decrease in optical activity was observed in solution, most likely due to racemization by homolytic (O)S-S(O) bond cleavage and bissulfinyl radical recombination.

AB - The trans isomer of 2,7-di-tert-butylnaphtho[1,8-cd][1,2]dithiole 1,2-dioxide, a vic-disulfoxide of the highest thermal stability reported to date, has been resolved into its enantiomers by preparative chiral liquid chromatography. This represents the first resolution achieved of a vic-disulfoxide. The absolute configuration of the isolated enantiomers has been determined to be (+)-(S,S), (-)-(R,R) from a comparison of experimental and calculated ECD and VCD spectra. The long-wavelength ECD band at about 330 nm had a positive sign in the (+)-(S,S)-form and a negative sign in the (-)-(R,R)-enantiomer. A photocatalyzed slow decrease in optical activity was observed in solution, most likely due to racemization by homolytic (O)S-S(O) bond cleavage and bissulfinyl radical recombination.

KW - Sulfur

KW - Circular dichroism

KW - Density functional calculations

KW - Configuration determination

U2 - 10.1002/ejoc.201100419

DO - 10.1002/ejoc.201100419

M3 - Article

SP - 4089

EP - 4092

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

SN - 1434-193X

IS - 22

ER -