Addition of thianthrene cation radical to non-conjugated dienes - Part II: Addition to two double bonds

Bing Jun Zhao, Henry J. Shine, John N. Marx, Anna T. Kelly, Cristina Hofmann, Teyeb Ould-Ely, Kenton H. Whitmire

Research output: Contribution to journal › Article

2 Citations (Scopus)

Abstract

Reaction of thianthrene cation radical tetrafluoroborate with 1,5-hexadiene, 1,7-octadiene, 1,8-nonadiene and 1,9-decadiene in the molar ratio 4:1 caused addition to occur to one and both of each diene's double bonds. A mixture of four adducts was thus obtained, namely a bisadduct (12a-d), a monoadduct (13a-d), a di(bis)adduct (14a-d) and a di(mono)adduct (15a-d). The di(mono)adducts (15b-d) were isolated and characterized with 1H and 13C NMR spectroscopy. Under the same condition of excess of cation radical, addition occurred to only one double bond of 1,4-cyclohexadiene and 1,5-cyclooctadiene. Addition to both double bonds was not observed. The bisadduct (16) of 1,4-cyclohexadiene was characterized with 1H and 13C NMR spectroscopy and X-ray crystallography. On activated alumina, 15b-d underwent fast opening of dicationic rings to form mixtures of (E, E)- (17b-d) and (E, Z)-di(5-thianthreniumyl)diene (18b-d) in which the (E, E)-isomer was dominant and was characterized with 1H and 13C NMR spectroscopy.

Original languageEnglish
Pages (from-to)139-147
Number of pages9
JournalJournal of Sulfur Chemistry
Volume27
Issue number2
DOIs
Publication statusPublished - Apr 2006
Externally publishedYes

Fingerprint

Nuclear magnetic resonance spectroscopy
Cations
Activated alumina
X ray crystallography
Isomers
thianthrene
1,4-cyclohexadiene
1,7-octadiene
1,5-hexadiene
1,9-decadiene
1,5-cyclooctadiene

Keywords

  • Adducts of dienes
  • NMR
  • Thianthrene cation radical

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Zhao, B. J., Shine, H. J., Marx, J. N., Kelly, A. T., Hofmann, C., Ould-Ely, T., & Whitmire, K. H. (2006). Addition of thianthrene cation radical to non-conjugated dienes - Part II: Addition to two double bonds. Journal of Sulfur Chemistry, 27(2), 139-147. https://doi.org/10.1080/17415990600578467

Addition of thianthrene cation radical to non-conjugated dienes - Part II : Addition to two double bonds. / Zhao, Bing Jun; Shine, Henry J.; Marx, John N.; Kelly, Anna T.; Hofmann, Cristina; Ould-Ely, Teyeb; Whitmire, Kenton H.

In: Journal of Sulfur Chemistry, Vol. 27, No. 2, 04.2006, p. 139-147.

Research output: Contribution to journal › Article

Zhao, BJ, Shine, HJ, Marx, JN, Kelly, AT, Hofmann, C, Ould-Ely, T & Whitmire, KH 2006, 'Addition of thianthrene cation radical to non-conjugated dienes - Part II: Addition to two double bonds', Journal of Sulfur Chemistry, vol. 27, no. 2, pp. 139-147. https://doi.org/10.1080/17415990600578467
Zhao BJ, Shine HJ, Marx JN, Kelly AT, Hofmann C, Ould-Ely T et al. Addition of thianthrene cation radical to non-conjugated dienes - Part II: Addition to two double bonds. Journal of Sulfur Chemistry. 2006 Apr;27(2):139-147. https://doi.org/10.1080/17415990600578467
Zhao, Bing Jun ; Shine, Henry J. ; Marx, John N. ; Kelly, Anna T. ; Hofmann, Cristina ; Ould-Ely, Teyeb ; Whitmire, Kenton H. / Addition of thianthrene cation radical to non-conjugated dienes - Part II : Addition to two double bonds. In: Journal of Sulfur Chemistry. 2006 ; Vol. 27, No. 2. pp. 139-147.
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abstract = "Reaction of thianthrene cation radical tetrafluoroborate with 1,5-hexadiene, 1,7-octadiene, 1,8-nonadiene and 1,9-decadiene in the molar ratio 4:1 caused addition to occur to one and both of each diene's double bonds. A mixture of four adducts was thus obtained, namely a bisadduct (12a-d), a monoadduct (13a-d), a di(bis)adduct (14a-d) and a di(mono)adduct (15a-d). The di(mono)adducts (15b-d) were isolated and characterized with 1H and 13C NMR spectroscopy. Under the same condition of excess of cation radical, addition occurred to only one double bond of 1,4-cyclohexadiene and 1,5-cyclooctadiene. Addition to both double bonds was not observed. The bisadduct (16) of 1,4-cyclohexadiene was characterized with 1H and 13C NMR spectroscopy and X-ray crystallography. On activated alumina, 15b-d underwent fast opening of dicationic rings to form mixtures of (E, E)- (17b-d) and (E, Z)-di(5-thianthreniumyl)diene (18b-d) in which the (E, E)-isomer was dominant and was characterized with 1H and 13C NMR spectroscopy.",
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AU - Marx, John N.

AU - Kelly, Anna T.

AU - Hofmann, Cristina

AU - Ould-Ely, Teyeb

AU - Whitmire, Kenton H.

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AB - Reaction of thianthrene cation radical tetrafluoroborate with 1,5-hexadiene, 1,7-octadiene, 1,8-nonadiene and 1,9-decadiene in the molar ratio 4:1 caused addition to occur to one and both of each diene's double bonds. A mixture of four adducts was thus obtained, namely a bisadduct (12a-d), a monoadduct (13a-d), a di(bis)adduct (14a-d) and a di(mono)adduct (15a-d). The di(mono)adducts (15b-d) were isolated and characterized with 1H and 13C NMR spectroscopy. Under the same condition of excess of cation radical, addition occurred to only one double bond of 1,4-cyclohexadiene and 1,5-cyclooctadiene. Addition to both double bonds was not observed. The bisadduct (16) of 1,4-cyclohexadiene was characterized with 1H and 13C NMR spectroscopy and X-ray crystallography. On activated alumina, 15b-d underwent fast opening of dicationic rings to form mixtures of (E, E)- (17b-d) and (E, Z)-di(5-thianthreniumyl)diene (18b-d) in which the (E, E)-isomer was dominant and was characterized with 1H and 13C NMR spectroscopy.

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